α-sulfenimino acid derivatives

ABSTRACT

α-Sulfenimino acid derivatives of formula I                    
     including the optical isomers thereof and mixtures of such isomers, wherein 
     A is cycloalkyl, cycloalkenyl, aryl or heteroaryl, each optionally substituted, 
     B is a direct bond or optionally substituted alkylene, 
     E is hydrogen or optionally substituted aryl, 
     R is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each optionally substituted, and 
     T is NH or oxygen, 
     have been found to be useful for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi. 
     The invention relates the novel compounds and also to the preparation thereof and to the use of the compounds for plant protection, and to compositions suitable for applying the novel compounds in agricultural techniques.

This application is a continuation of PCT/EP00/00247 Jan. 13, 2000.

The present invention relates to novel α-sulfenimino acid derivatives of formula I below. It relates to the preparation of those substances and to agrochemical compositions comprising at least one of those compounds as active ingredient. The invention relates also to the preparation of the said compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

The invention relates to α-sulfenimino acid derivatives of the general formula I

including the optical isomers thereof and mixtures of such isomers, wherein

A is cycloalkyl, cycloalkenyl, aryl or heteroaryl, each optionally substituted,

B is a direct bond or optionally substituted alkylene,

E is hydrogen or optionally substituted aryl,

R is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each optionally substituted, and

T is NH or oxygen.

In the above definition aryl includes aromatic hydrocarbon rings like phenyl, naphthyl, anthracenyl, phenanthrenyl, with phenyl being preferred. Heteroaryl stands for aromatic ring systems comprising mono-, bi- or tricyclic systems wherein at least one oxygen, nitrogen or sulfur atom is present as a ring member. Examples are furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.

The above alkyl, alkenyl, alkynyl, cycloalkyl, aryl and heteroaryl groups may carry one or more identical or different substituents. Normally not more than three substituents in each of these groups are present at the same time.

Preferred subgroups of the compounds of formula I are those wherein

A is phenyl, naphthyl, cycloalkyl, cycloalkenyl or mono- or bicyclic heteroaryl comprising five- or six-membered rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur, wherein each of the cycles is optionally mono- or poly-substituted by substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkyn-yloxy, C₃₋₈-cycloalkyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkanoyloxy, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkenyloxycarbonyl, C₃₋₈-alkynyloxycarbonyl, C₁₋₈-dialkylamino, C₁₋₈-alkylamino, C₁₋₈-hydroximinoalkyl and C₁₋₈-alkoximinoalkyl, wherein each of the alkyl, alkenyl, alkynyl moieties are straight-chain or branched and may in turn be optionally halogenated; halogen; nitro; cyano; hydroxy; amino; formyl; carboxyl; carbamoyl and thiocarbamoyl; or from the group comprising aryl, aryloxy, arylthio, aryl-C₁₋₄-alkyl, aryl-C₁₋₄-alkyloxy, aryl-C₁₋₄-alkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclyl-C₁₋₄-alkyl, heterocyclyl-C₁₋₄-alkoxy and heterocyclyl-C₁₋₄-alkylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl comprises mono- or bicyclic five- or six-membered non-aromatic and aromatic rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur; or from the group comprising aryloxyalkyl, aryloxyheteroaryloxy, heteroaryloxyalkyl, arylalkyliminoxyalkyl, aryloxyiminoalkyl, arylalkyloxyiminoalkyl, aryloxyiminoalkyleniminoxyalkyl and aryl-alkyloxy-iminoalkyleniminoxyalkyl wherein each alkyl or alkylene may be straight-chain or branched and each alkyl, alkylene, aryl or heteroaryl may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy, C₁₋₄-alkylthio or phenyl or phenoxy wherein the phenyl moieties are optionally substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; or

A is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzthiazolyl, chinolinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, aryl-C₁₋₄-alkyl, aryl-C₁₋₄-alkyloxy, aryl-C₁₋₄-alkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclyl-C₁₋₄-alkyl, heterocyclylC₁₋₄-alkoxy and heterocyclyl-C₁₋₄-alkylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl is furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzthiazolyl, chinolinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl; or from the group comprising phenoxy-C₁₋₄-alkyl, phenoxyheteroaryloxy, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each alkyl, alkylene, phenyl or phenoxy in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy, C₁₋₄-alkylthio or phenyl or phenoxy wherein the phenyl moieties are optionally substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy or C₁₋₄-alkylthio; or

A is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy and heterocyclylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl is furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl, indolyl or pyrrolyl; or from a group comprising phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy or C₁₋₄-alkylthio; or

A is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl or pyrrolyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₄-alkyl, C₂₋₆-alkenyl, C₃₋₆-cycloalkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-alkoxycarbonyl, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy and heterocyclylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl is furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl, indolyl or pyrrolyl; or

B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising halogen, linear or branched C₁₋₆-alkyl, C₂₋₆-alkenyl or C₂₋₆-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; or

B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising F, Cl, Br, linear or branched C₁₋₄-alkyl, C₂₋₄-alkenyl or, C₂₋₄-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; or

B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising F, Cl, Br, linear or branched C₁₋₂-alkyl, C₂₋₃-alkenyl or, C₂₋₃-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; or

B is a direct bond, methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or 2,2-propylene; or

E is hydrogen or phenyl optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-cycloalkyloxy, C₆₋₁₀-aryloxy, C₆₋₁₀-aryl-C₁₋₆-alkyloxy, C₆₋₁₀-aryl-C₃₋₆-alkenyloxy, C₆₋₁₀-aryl-C₃₋₆-alkynyloxy, C₃₋₈cycloalkyl-C₃₋₆alkynyloxy, C₁₋₈-alkanoyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkinyloxycarbonyl and C₃₋₈-alkinyloxycarbonyl wherein in each of the preceding groups the alkyl, alkenyl, alkynyl or cycloalkyl part may be partially or fully halogenated and wherein the aryl groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; halogen, nitro, cyano, hydroxy, amino, di-C₁₋₈-alkylamino and C₁₋₈-alkylamino; or

E is hydrogen or phenyl optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, phenyl-C₁₋₆-alkyloxy, phenyl-C₃₋₆-alkenyloxy, phenyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₃₋₈cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxy, C₃₋₈-haloalkenyloxy, halogen and cyano, wherein the phenyl groups may be optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; or

E is hydrogen or phenyl optionally di- to tri-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, phenyl-C₁₋₆-alkyloxy, phenyl-C₃₋₆-alkenyloxy, phenyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₃₋₈cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxy, C₃₋₈-haloalkenyloxy, halogen and cyano, wherein the phenyl groups may be optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; or

E is hydrogen or a group

 wherein R₂ is C₁₋₄-alkyl, and R₃ is C₁₋₈-alkyl, C₃₋₈-alkenyl, C₃₋₈-alkynyl, phenyl-C₁₋₆-alkyl, phenyl-C₃₋₆-alkenyl, phenyl-C₃₋₆-alkynyl, C₃₋₈cycloalkyl-C₃₋₆-alkynyl, C₁₋₈-halogenalkyl or C₃₋₈-halogenalkenyl wherein in each of the preceding radicals the phenyl groups may be optionally substituted with 1 to 3 substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; or

R is hydrogen or C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₆₋₁₀-aryl or C₆₋₁₀-aryl-C₁₋₆-alkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₆-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkenyloxycarbonyl and C₃₋₈-alkynyloxycarbonyl wherein each of the alkyl, alkenyl, alkynyl or cycloalkyl parts of the preceding substituents may be partially or fully halogenated; halogen, nitro and cyano; or

R is C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl or C₃₋₈-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or

R is C₁₋₆-alkyl, C₂₋₆-alkenyl or C₅₋₆-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkoxycarbonyl, C₁₋₄-haloalkyl, halogen and cyano; or

R is straight-chain or branched C₁₋₄-alkyl, C₂₋₆-alkenyl or C₅₋₆-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with F, Cl or Br.

Examples of substituents of cycloalkyl, cycloalkenyl, aryl or heteroaryl groups are: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenyl-alkyl, it being possible in turn for all of the preceding groups to carry one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy, alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl; alkynyloxycarbonyl.

In the above definitions “halogen” includes fluorine, chlorine, bromine and iodine.

The alkyl, alkenyl and alkynyl radicals may be straight-chain or branched. This applies also to the alkyl, alkenyl or alkynyl parts of other alkyl-, alkenyl- or alkynyl-containing groups.

Depending upon the number of carbon atoms mentioned, alkyl on its own or as part of another substituent is to be understood as being, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the isomers thereof, for example isopropyl, isobutyl, tert-butyl or sec-butyl, isopentyl or tert-pentyl.

Cycloalkyl is, depending upon the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Cycloalkenyl preferably includes cyclopentenyl, cyclohexenyl and cycloheptenyl; the double bond being in any possible position of the ring including the binding position.

The alkylene bridge under the definition of B may be straight chain or branched. Preferred embodiments are 1,2-ethylene and 1,2-propylene.

Depending upon the number of carbon atoms mentioned, alkenyl as a group or as a structural element of other groups is to be understood as being, for example, ethenyl, allyl, 1-propenyl, buten-2-yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl, 4-methyl-3-pentenyl or 4-methyl-3-hexenyl.

Alkynyl as a group or as a structural element of other groups is, for example, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl, 1-methyl-2-butynyl, hexyn-1-yl, 1-ethyl-butynyl or octyn-1-yl.

A haloalkyl group may contain one or more (identical or different) halogen atoms, and for example may stand for CHCl₂, CH₂F, CCl₃, CH₂Cl, CHF₂, CF₃, CH₂CH₂Br, C₂Cl₅, CH₂Br, CHClBr, CF₃CH₂, etc.

The presence of at least one asymmetric carbon atom and/or at least one asymmetric oxidized sulfur atom in the compounds of formula I means that the compounds may occur in optically isomeric forms. As a result of the presence of a possible aliphatic C═C and C═N double bond, geometric isomerism may also occur. Formula I is intended to include all those possible isomeric forms and mixtures thereof.

Further preferred subgroups of the compounds of formula I are those wherein

A is phenyl, naphthyl, cycloalkyl, cycloalkenyl or mono- or bicyclic heteroaryl comprising five- or six-membered rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur, wherein each of the cycles is optionally mono- or poly-substituted by substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-cycloalkyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkanoyloxy, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkenyloxycarbonyl, C₃₋₈-alkynyloxycarbonyl, C₁₋₈-dialkylamino, C₁₋₈-alkylamino, C₁₋₈-hydroximinoalkyl and C₁₋₈-alkoximinoalkyl, wherein each of the alkyl, alkenyl, alkynyl moieties are straight-chain or branched and may in turn be optionally halogenated; halogen; nitro; cyano; hydroxy; amino; formyl; carboxyl; carbamoyl and thiocarbamoyl; or from the group comprising aryl, aryloxy, arylthio, aryl-C₁₋₄-alkyl, aryl-C₁₋₄-alkyloxy, aryl-C₁₋₄-alkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclyl-C₁₋₄-alkyl, heterocyclyl-C₁₋₄-alkoxy and heterocyclyl-C₁₋₄-alkylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl comprises mono- or bicyclic five- or six-membered non-aromatic and aromatic rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur; or from the group comprising aryloxyalkyl, heteroaryloxyalkyl, arylalkyliminoxyalkyl, aryloxyiminoalkyl, arylalkyloxyiminoalkyl, aryloxyiminoalkyleniminoxyalkyl and aryl-alkyloxyiminoalkylen-iminoxyalkyl wherein each alkyl or alkylene may be straight-chain or branched and each aryl or heteroaryl may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising halogen, linear or branched C₁₋₆-alkyl, C₂₋₆-alkenyl or C₂₋₆-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; and E is hydrogen or phenyl optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-cycloalkyloxy, C₆₋₁₀-aryloxy, C₆₋₁₀-aryl-C₁₋₆-alkyloxy, C₆₋₁₀-aryl-C₃₋₆-alkenyloxy, C₆₋₁₀-aryl-C₃₋₆-alkynyloxy, C₁₋₈-alkanoyloxy, C₃₋₈cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkinyloxycarbonyl and C₃₋₈-alkinyloxycarbonyl wherein in each of the preceding groups the alkyl, alkenyl, alkynyl or cycloalkyl part may be partially or fully halogenated and wherein the aryl groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; halogen, nitro, cyano, hydroxy, amino, di-C₁₋₈-alkylamino and C₁₋₈-alkylamino; and R is hydrogen or C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₆₋₁₀-aryl or C₆₋₁₀-aryl-C₁₋₆-alkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkenyloxycarbonyl and C₃₋₈-alkynyloxycarbonyl wherein each of the alkyl, alkenyl, alkynyl or cycloalkyl parts of the preceding substituents may be partially or fully halogenated; halogen, nitro and cyano; or

A is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzthiazolyl, chinolinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, aryl-C₁₋₄-alkyl, aryl-C₁₋₄-alkyloxy, aryl-C₁₋₄-alkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclyl-C₁₋₄-alkyl, heterocyclyl-C₁₋₄-alkoxy and heterocyclyl-C₁₋₄-alkylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl is furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzthiazolyl, chinolinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl; or from the group comprising phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising F, Cl, Br, linear or branched C₁₋₄-alkyl, C₂₋₄-alkenyl or, C₂₋₄-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; and E is hydrogen or phenyl optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, phenyl-C₁₋₆-alkyloxy, phenyl-C₃₋₆-alkenyloxy, phenyl-C₃₋₆-alkynyloxy, C₃₋₈cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxy, C₃₋₈-haloalkenyloxy, halogen and cyano, wherein the phenyl groups may be optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; and R is C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl or C₃₋₈-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or

A is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy and heterocyclylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl is furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl, indolyl or pyrrolyl; or from a group comprising phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising F, Cl, Br, linear or branched C₁₋₂-alkyl, C₂₋₃-alkenyl or, C₂₋₃-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; and E is hydrogen or phenyl optionally di- to tri-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, phenyl-C₁₋₆-alkyloxy, phenyl-C₃₋₆-alkenyloxy, phenyl-C₃₋₆-alkynyloxy, C₃₋₈cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxy, C₃₋₈-haloalkenyloxy, halogen and cyano, wherein the phenyl groups may be optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; and R is C₁₋₆-alkyl, C₂₋₆-alkenyl or C₅₋₆-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkoxycarbonyl, C₁₋₄-haloalkyl, halogen and cyano; or

A is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl or pyrrolyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₄-alkyl, C₂₋₆-alkenyl, C₃₋₆-cycloalkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-alkoxycarbonyl, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy and heterocyclylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio, wherein heterocyclyl is furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, pyrazolyl, indolyl or pyrrolyl; and B is a direct bond, methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or 2,2-propylene; and E is hydrogen or a group

 wherein R₂ is C₁₋₄-alkyl, and R₃ is C₁₋₈-alkyl, C₃₋₈-alkenyl, C₃₋₈-alkynyl, phenyl-C₁₋₆-alkyl, phenyl-C₃₋₆-alkenyl, phenyl-C₃₋₆-alkynyl, C₃₋₈cycloalkyl-C₃₋₆-alkynyl, C₁₋₈-halogenalkyl or C₃₋₈-halogenalkenyl wherein in each of the preceding radicals the phenyl groups may be optionally substituted with 1 to 3 substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; and R is straight-chain or branched C₁₋₄-alkyl, C₂₋₆-alkenyl or C₅₋₆-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with F, Cl or Br; and T is NH; or

A is phenyl, naphthyl, cycloalkyl, cycloalkenyl or mono- or bicyclic heteroaryl comprising five- or six-membered rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur, wherein each of the cycles is optionally substituted by substituents selected from the group comprising aryloxyalkyl, heteroaryloxyalkyl, aryloxy-heteroaryloxy, arylalkyliminoxyalkyl, aryloxyiminoalkyl, arylalkyloxyiminoalkyl, aryloxyiminoalkyleniminoxyalkyl and aryl-alkyloxyiminoalkyleniminoxyalkyl wherein each alkyl or alkylene may be straight-chain or branched and each alkyl, alkylene, aryl or heteroaryl may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄haloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy, or C₁₋₄-alkylthio; and B is a direct bond or C₁₋₄-alkylene; and E is hydrogen; and R is hydrogen or C₁₋₁₀-alkyl; or

A is phenyl, thienyl, imidazolyl, pyridyl, pyrimidinyl, pyrazolyl or pyrrolyl, each optionally-substituted by a substituent selected from the group comprising phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is C₁₋₄-alkylene; and E is hydrogen; and R is straight-chain or branched C₁₋₄-alkyl; or

A is phenyl substituted by phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl or phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is methylene; and E is hydrogen; and R is methyl or ethyl.

Preferred individual compounds are:

2-(3,4-dichloro-phenyl)-N-[2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

N-[2-(4-allyloxy-3-methoxy-phenyl)-ethyl]-2-(3,4-dichloro-phenyl)-2-methylthioimino-acetamide,

N-[2-(3-methoxy-4-prop-ynyloxy-phenyl)-ethyl]-2-methylthioimino-2-(4-tolyl)-acetamide,

2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

N-[2-(3-methoxy-4-prop-ynyloxy-phenyl)-ethyl]-2-naphthalen-2-yl-2-methylthioimino-2-acetamide,

2-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-(4-methoxy-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

N-[2-(3-methoxy-4-prop-ynyloxy-phenyl)-ethyl]-2-(3,4-dichloro-phenyl)-2-ethylthioimino-2-(4-tolyl)-acetamide,

N-methyl-2-methylthioimino-2-{2-[1-(trifluoromethyl-phenyl)-ethylideneaminooxymethyl]-phenyl}-acetamide,

2-methylthioimino-2-{2-[1-(trifluoromethyl-phenyl)-ethylideneaminooxymethyl]-phenyl}-acetic acid methyl ester,

2-{2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-N-methyl-2-methylthioimino-acetamide,

2-{2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-2-methylthioimino-acetic acid methyl ester,

2-[4-(4-methyl-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-[4-(3,4-dichloro-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-[4-(4-chloro-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-[4-(4-trifluoromethyl-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide,

2-[4-(4-trifluoromethoxy-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthio-imino-acetamide,

2-[4-(4-tert.-butyl-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide and,

2-(4-biphenylyl)-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide.

The α-sulfenimino acid derivatives of formula I may be obtained according to one of the following processes:

Step A: A α-hydroxy acid of formula II or a α-keto-acid of the formula V wherein A is as defined for formula I, is reacted at a temperature between +150° C. and +250° C. in the presence of an excess of an alcohol or amine of formula III, wherein B, E and T are as defined for formula I, and in the presence of an acidic catalyst as p-toluenesulfonic acid.

The reaction conditions correspond to those known for esterifications and amidations, e.g. as described in WO 94/29267. Alternatively, the acids compounds of formulae II or V may be transformed to amides of formulae IV or VI in the presence of activating reagents as e.g. described below for the process b) of Step D.

Step B: The α-hydroxy acid of formula II or the α-hydroxy acid derivative of formula IV where A, E, B and T are as defined for formula I, is oxidized by reaction with an organic oxidizing agent (e.g. an alkyl hydroperoxyde, a DMSO-based reagent as described by T. T. Tidwell, Org. React., 1990, 39, 297-572, a hypervalent iodine reagent, a dioxirane, a nitroxyl radical, or an inorganic oxidizing agent (e.g. peroxides, hypochlorites, transition metal oxide of e.g. Cr, Mn, Ru, Re, Os, sodium percarbonate, sodium perborate, silver carbonate).

The oxidation reaction is preferably conducted in an inert solvent, such as THF, CH₂Cl₂, water or a ketone, for example acetone, or in a mixtures thereof, in the absence or in the presence of an acid or in the presence or in the absence of a base, at temperatures between −80° C. +150° C.

Step C: A dioxolanone of the formula VII wherein A is as defined for formula I and R₄ and R₅ independently of each are hydrogen, C₁-C₈-alkyl or C₁-C₈-haloalkyl or R₄ and R₅ together with the carbon atom to which they are attached may form a 5-, 6- or 7-membered saturated, partially unsaturated or unsaturated isocyclic ring is reacted with an alcohol or amine of formula III, wherein B, E and T are as defined for formula I.

The reaction conditions are in analogy to known procedures (e.g. A. Khalaj, E. Nahid, Synthesis, 1985, 1153). The reaction is carried out in an inert solvent, e.g. toluene, xylene, THF, chlorobenzene hexane or heptane, at temperature between 0° C. and +200° C.

Step D: An α-keto acid derivative of formula VI, wherein A, B, E and T are as defined for formula I, is treated with a N, N-bis(silyl)sulfenamide of the formula VIII, where R is as defined for formula I, (c.f. T. Morimoto, Y. Nezu, K. Achiwa, M. Sekiya, J. Chem. Soc. Chem. Commun. 1985, 1584) in an inert solvent as THF, ether, glyme, at temperature between −40 and +150° C. in the presence of a catalyst, e.g. fluoride source as tert.-butylammonium fluoride, HF, KF or LiBF₄ and/or in the presence or in the absence of an acid, a Lewis acid or a base.

In alternative routes of conducting the above scheme a) the α-hydroxy acid of formula II and of the α-keto acid of formula V may first be converted into the activated forms of the acids, e.g. into lower esters or acid halides of formulae IX and X wherein Y is alkoxy, benzyloxy, phenoxy, F, Cl, or Br, by reacting II or V with lower alcohols (typically methanol, ethanol, propanol, isopropanol, butanol, sec-butanol, tert-butanol, phenol, benzylalcohol) or with a halogenating agent to form acid halides (fluorides, chlorides or bromides).

The reaction conditions for the formation of the activated derivatives IX and X are as commonly known for esterification or halogenation steps.

Step B: procedure is the same as in step B of process a). Y′ is as defined for Y for formulae IX or X in Scheme a) or is OH.

Step C: procedure is the same as in step D of process a). Y′ is as defined for Y for formulae IX or X in Scheme a) or is OH.

Step D: compounds of formula XI′ (A and R are as defined for formula I and Y′ is as defined for Y for formulae IX or X in scheme a) or is OH ) are treated with an alcohol or an amine of formula III, wherein B, E and T are as in formula I, in an inert solvent or without solvent in the presence or in the absence of an acid scavenger (e.g. a base as Na-alcoholate, K-alcoholate, triethylamine, diethyl-isopropylamine) at temperatures between −20° C. and +200° C., preferably at reflux temperature in alcohols.

Step D may become of special importance in those cases wherein the radical —T—B—E is sensitive to the thioiminolation reagent of formula VIII. Also compounds of the subformula Ia wherein T is NH are advantageously made from the activated compounds of formula XI by the procedure of step D.

Where Y′ is OH this step may further be facilitated by converting the acid function into an activated carboxyl group like an acid halide (halide=fluoride, chloride, bromide), like symmetrical or mixed anhydrides, such as mixed anhydrides with O-alkylcarbonates, like activated esters, such as p-nitrophenylesters or N-hydroxysucinimidesters, as well as in situ produced activated forms with condensating agents, such as dicyclohexylcarbodiimid, carbonyldiimidazol, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, O-benzotriazol-1-yl N,N,N′,N′-bis(pentamethylene)uronium hexafluorophosphate, O-benzotriazol-1-yl N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate, O-benzotriazol-1-yl N,N,N′,N′-tetramethyluronium hexafluorophosphate or benzotriazol-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate. The mixed anhydrides can be prepared by reaction of compounds of formula XI′ wherein Y′ is OH with chloroformic acid esters like chloroformic acid alkylesters, such as ethyl chloroformate or isobutyl chloroformate, optionally in the presence of an organic or inorganic base like a tertiary amine, such as triethylamine, N,N-diisopropyl-ethylamine, pyridine, n-methyl-piperidine or N-methyl-morpholin. The reaction is performed in a solvent like aromatic, non-aromatic or halogenated hydrocarbons, such as chlorohydrocarbons e.g. dichloromethane or toluene; ketones e.g. acetone; esters e.g. ethyl acetate; amides e.g. N,N-dimethylformamide; nitriles e.g. acetonitrile; or ethers e.g. diethylether, tert-butyl-methylether, dioxane or tetrahydrofurane. It is also possible to use mixtures of these solvents. The reaction may be performed optionally in the presence of an organic or inorganic base like NaH, KH, a tertiary amine, such as triethylamine, N,N-diisopropyl-ethylamine, pyridine, n-methyl-piperidine or N-methyl-morpholin at temperatures ranging from −80° C. to +150° C., preferably at temperatures ranging from −40° C. to +40° C.

Step A: A compound of formula VI wherein A, B, E and T are as defined for in formula I is transformed to a compound of formula XII under standard oximation conditions as described in J. March, Advanced Organic Chemistry, 4th ed., Wiley, 1992.

Step B: A compound of formula VI wherein A, B, E and T are as defined for in formula I is reacted with LG—O—NH₂, where LG is a leaving group, typically tosyl or mesyl, under classical oximation conditions as described by e.g. J. March, Advanced Organic Chemistry, 4th ed., Wiley, 1992 to give a compound of formula XIII wherein A, B, E and T are as defined for formula I.

Step C: An oxime of the formula XII wherein A, B, E and T are as defined for in formula I is reacted with LG-Hal, where Hal is a halogen, typically F, Cl, Br, or OH and LG a leaving group as defined above. The reaction conditions are as for the esterification or amidation process used in step D of process b).

Step D: A compound of formula XIII, wherein A, B, E and T are as defined for in formula I and LG is as defined above is reacted with a compound of the formula R—S—M wherein R is as defined for formula I and M is a alkaline metal cation such as Li, Na or K in an inert solvent (e.g. THF, DMF, glyme, diglyme) and in the presence of a base (e.g. tertiary amines like triethylamine or ethyl-dipropylamine, or alcoholates) at a temperature between +20° C. and +150° C. to give the compound of formula I.

Compounds of formula Xi are partly encompassed in formula I. Those compounds wherein Y is an alcoholic moiety are encompassed within formula I and exhibit favourable biological activities. Those compounds of formula XI′ wherein Y′ is halogen or OH serve as intermediates in the synthesis.

For compounds of formula I wherein T is NH also the following synthesis passway is suitable:

Step A: A N-formylamine of the formula XV wherein B and E are as defined for in formula I is dehydrated to an isocyanide of formula XVI under known conditions, as described e.g. in D. Seebach, G. Adam, T. Gees, M. Schiess, W. Weigang, Chem. Ber. 1988, 121, 507.

Step D B: An isocyanide of formula XVI wherein B and E are as defined for formula I, is reacted with an aldehyde of formula XIV, wherein A is as in formula I in the presence of a carboxylic acid (typically acetic acid) to give a O-acyl-α-hydroxy amide of formula XVII wherein A, B and E are as defined for in formula I and Alkyl is lower alkyl, preferably methyl.

The reaction conditions for this so-called “three-component-Passerini-Reaction are described in J. March, Advanced Organic Chemistry, 4th ed., Wiley, 1992, p. 980.

Alternatively an isocyanide of formula XVI wherein B and E are as defined for formula I is reacted with an aldehyde of formula XIV in the presence of titanium tetrachloride to give directly the α-hydroxy amide of the formula IVa wherein A, B and E are as defined for in formula I. The principle reaction conditions are similar to those described in Chem. Ber. 1988, 121, 507; and O. Ort et al. Pesticide Sci. 1997, 50, 331.

Step C: A N-formylamine of formula XV wherein B and E are as defined for formula I is treated with a phosgene equivalent (e.g. triphosgene) and a base (e.g. triethylamine) and in a second step without isolation of the isocyanide intermediate is further treated with titanium tetrachloride and an aldehyde of formula XIV wherein A is as in formula I. Reaction conditions for such reaction are as the conditions in WO 96/17840. In the resulting α-hydroxy amide of the formula IVa the radicals A, B and E are as in formula I.

Step D: An O-acyl-α-hydroxy amide of formula XVII is saponified to a an α-hydroxy amide of formula IVa under classical conditions for hydrolysis (c.f. to e.g. J. March, Advanced Organic Chemistry, 4th ed., Wiley, 1992).

Step E: same conditions as in step B of process a).

Step F: same conditions as in step D of process a).

The compounds of formula I are oils or solids at room temperature and are distinguished by valuable microbicidal properties. They can be used in the agricultural sector or related fields preventively and curatively in the control of plant-destructive microorganisms. The compounds of formula I according to the invention are distinguished at low rates of concentration not only by outstanding microbicidal, especially fungicidal, activity but also by being especially well tolerated by plants.

Surprisingly, it has now been found that the compounds of formula I have for practical purposes a very advantageous biocidal spectrum in the control of phytopathogenic micro-organisms, especially fungi. They possess very advantageous curative and preventive properties and are used in the protection of numerous crop plants. With the compounds of formula I it is possible to inhibit or destroy phytopathogenic microorganisms that occur on various crops of useful plants or on parts of such plants (fruit, blossom, leaves, stems, tubers, roots), while parts of the plants which grow later also remain protected, for example, against phytopathogenic fungi.

The novel compounds of formula I prove to be effective against specific genera of the fungus class Fungi imperfecti (e.g. Cercospora), Basidiomycetes (e.g. Puccinia) and Ascomycetes (e.g. Erysiphe and Venturia) and especially against Oomycetes (e.g. Plasmopara, Peronospora, Pythium and Phytophthora). They therefore represent in plant protection a valuable addition to the compositions for controlling phytopathogenic fungi. The compounds of formula I can also be used as dressings for protecting seed (fruit, tubers, grains) and plant cuttings from fungal infections and against phytopathogenic fungi that occur in the soil.

The invention relates also to compositions comprising compounds of formula I as active ingredient, especially plant-protecting compositions, and to the use thereof in the agricultural sector or related fields.

In addition, the present invention includes the preparation of those compositions, wherein the active ingredient is homogeneously mixed with one or more of the substances or groups of substances described herein. Also included is a method of treating plants which is distinguished by the application of the novel compounds of formula I or of the novel compositions.

Target crops to be protected within the scope of this invention comprise, for example, the following species of plants: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, stone fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucurbitaceae (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamon, camphor) and plants such as tobacco, nuts, coffee, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, and also ornamentals.

The compounds of formula I are normally used in the form of compositions and can be applied to the area or plant to be treated simultaneously or in succession with other active ingredients. Those other active ingredients may be fertilisers, micronutrient donors or other preparations that influence plant growth. It is also possible to use selective herbicides or insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of those preparations, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology.

The compounds of formula I can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities.

Mixing components which are particularly preferred are azoles such as azaconazole, bitertanol, propiconazole, difenoconazole, diniconazole, cyproconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, tebuconazole, tetraconazole, fenbuconazole, metconazole, myclobutanil, perfurazoate, penconazole, bromuconazole, pyrifenox, prochloraz, triadimefon, triadimenol, triflumizole or triticonazole; pyrimidinyl carbinoles such as ancymidol, fenarimol or nuarimol; 2-amino-pyrimidine such as bupirimate, dimethirimol or ethirimol; morpholines such as dodemorph, fenpropidin, fenpropimorph, spiroxamin or tridemorph; anilinopyrimidines such as cyprodinil, pyrimethanil or mepanipyrim; pyrroles such as fenpiclonil or fludioxonil; phenylamides such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace or oxadixyl; benzimidazoles such as benomyl, carbendazim, debacarb, fuberidazole or thiabendazole; dicarboximides such as chlozolinate, dichlozoline, iprodine, myclozoline, procymidone or vinclozolin; carboxamides such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin or thifluzamide; guanidines such as guazatine, dodine or iminoctadine; strobilurines such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, methyl 2-[(2-trifluoromethyl)-pyrid-6-yloxymethyl]-3-methoxyacrylate or 2-[α{[(α-methyl-3-trifluoromethyl-benzyl)imino]-oxy}-o-tolyl]-glyoxylic acid-methylester-O-methyloxime (trifloxystrobin); dithiocarbamates such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb or ziram; N-halomethylthio-dicarboximides such as captafol, captan, dichlofluanid, fluoromide, folpet or tolyfluanid; copper compounds such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper or oxine-copper; nitrophenol derivatives such as dinocap or nitrothal-isopropyl; organo phosphorous derivatives such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos or toclofos-methyl; and other compounds of diverse structures such as acibenzolar-S-methyl, anilazine, blasticidin-S, chinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etridiazole, famoxadone, fenamidone, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, kasugamycin, methasulfocarb, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin, (S)-5-methyl-2-methylthio-5-phenyl-3-phenyl-amino-3,5-dihydroimidazol-4-one (RPA 407213), 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281), N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide (MON 65500), 4-chloro-4-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916), N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)-propionamide (AC 382042), or iprovalicarb (SZX 722).

Suitable carriers and surfactants may be solid or liquid and correspond to the substances ordinarily employed in formulation technology, such as e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilisers. Such carriers and additives are described, for example, in WO 95/30651.

A preferred method of applying a compound of formula I, or an agrochemical composition comprising at least one of those compounds, is application to the foliage (foliar application), the frequency and the rate of application depending upon the risk of infestation by the pathogen in question. The compounds of formula I may also be applied to seed grains (coating) either by impregnating the grains with a liquid formulation of the active ingredient or by coating them with a solid formulation.

The compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in formulation technology, and are for that purpose advantageously formulated in known manner e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and by encapsulation in e.g. polymer substances. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

Advantageous rates of application are normally from 1 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, especially from 25 g to 750 g a.i./ha. When used as seed dressings, rates of from 0.001 g to 1.0 g of active ingredient per kg of seed are advantageously used.

The formulations, i.e. the compositions, preparations or mixtures comprising the compound(s) (active ingredient(s)) of formula I and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredient with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

Further surfactants customarily used in formulation technology will be known to the person skilled in the art or can be found in the relevant technical literature.

The agrochemical compositions usually comprise 0.01 to 99% by weight, preferably 0.1 to 95% by weight, of a compound of formula I, 99.99 to 1% by weight, preferably 99.9 to 5% by weight, of a solid or liquid adjuvant, and 0 to 25% by weight, preferably 0.1 to 25% by weight, of a surfactant.

Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The compositions may also comprise further ingredients, such as stabilisers, antifoams, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients for obtaining special effects.

The Examples which follow illustrate the invention described above, without limiting the scope thereof in any way. Temperatures are given in degrees Celsius.

PREPARATION EXAMPLES FOR COMPOUNDS OF FORMULA I Example 1 2-(3,4-Dichloro-phenyl)-2-methylthioimino-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide

a) N-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-formamide

50 g (256 mmol) trans-2-methoxy-4-(2-nitrovinyl)phenol are hydrogenated in 1.5 I EtOH and 63.1 g HCl 37% with 30 g Pd/C (10%) at normal pressure and from −18° C. to +3520 C. The solution is filtrated on Cellite and recrystallised from EtOH/ether. 41.6 g (80%) product is isolated.

65.6 g (323 mmol) of the same product is dissolved in 1050 ml MeOH and treated with 48 ml (347 mmol) triethylamine and 1650 ml ethyl formiate. The clear solution is refluxed for 22 hours. After evaporation, flash-chromatography of the residue and crystallisation in ether, 42.6 g (68%) N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-formamide is isolated. ¹H-NMR (300 MHz, CDCl₃): 2.79 (m, 2 H, CH₂CH₂), 3.45 and 3.56 (2 q, (17:83), 2 H, CH₂CH₂), 3.89 (s, 3 H, OCH₃), 5.55-5.68 (m, 2 H, NH, OH), 6.69 and 6.86, 2 m, 3 H, arom.), 8.15 (s, 1 H, CHO).

b) N-[2-(3-Methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-formamide

41 ml NaOMe 30% in methanol are added to a solution of 31.5 g (180 mmol) N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-formamide in 880 ml methanol. 48.1 g (184 mmol) toluene-4-sulfonic acid pent-2-ynyl ester are added and the mixture is refluxed for 4 hours. After evaporation the residue is taken up in ethyl acetate and washed with water. After evaporation the residue is submitted to flash-chromatography and crystallisation in ether to give 27.8 g (61%) of the N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-formamide. ¹H-NMR (300 MHz, CDCl₃): 1.14 (t, 3 H, CH₂CH₃), 2.22 (m, 2 H, CH₂CH₃), 2.81 (t, 2 H, CH₂CH₂), 3.48 and 3.57 (2 q (17:83), 2 H, CH₂CH₂), 3.88 (s, 3 H, OCH₃), 4.70 (m, 2 H, OCH₂), 5.58 (b, 1 H, NH), 6.73 (m, 2 H, arom.), 6.98 (m, 1 H, arom.), 8.14 (s, 1 H, CHO).

c) 2-(3,4-Dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide

3.4 g (13.0 mmol) N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-formamide and 4.3 ml (32 mmol) triethylamine are dissolved in 13 ml CH₂Cl₂. 1.4 g (4.7 mmol) bis(trichloromethyl) carbonate (triphosgene) in 9 ml CH₂Cl₂ is added at +5° C. The mixture is stirred 4 hours at +5° C. and then cooled to −78° C. A solution of 1.43 ml (13.0 mmol) TiCl₄ in 20 ml CH₂Cl₂ is added and the mixture is stirred for 2 hours at −40° C. 2.5 g (12.9 mmol) 3,4-dichloro-benzaldehyde in 7 ml CH₂Cl₂ is added dropwise and the mixture stirred for 17 hours at +20° C. The mixture is hydrolysed with 7 ml HCl 5N, stirred 30 minutes at +20° C. and washed with water. After evaporation the residue is submitted to flash-chromatography (ethyl acetate 6, hexanes 4) to give 2.7 g (48%) of the 2-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide. ¹H-NMR (300 MHz, CDCl₃): 1.15 (t, 3 H, CH₂CH₃), 2.22 (m, 2 H, CH₂CH₃), 2.75 (t, 2 H, CH₂CH₂), 3.51 (m, 2 H, CH₂CH₂), 3.69 (d, 2 H, OH), 3.83 (s, 3 H, OCH₃), 4.74 (m, 2 H, OCH2), 4.96 (d, 1 H, CHOH), 6.27 (t, 1 H, NH), 6.58 (m, 1 H), 6.68 (m, 1 H), 6.92 (d, 1 H), 7.19 (d, 1 H), 7.42 (d, 1 H) and 7.49 (m, 1 H, CH arom.).

d) 2-(3,4-Dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide

To a solution of 0.8 ml oxalyl chloride (9.0 mmol) in 8 ml methylenchloride at −63° C is added in 15 minutes a solution of 0.84 ml DMSO (12.0 mmol) in 4 ml CH₂Cl₂. A solution of 2.6 g (6.0 mmol) of 2-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide in 30 ml CH₂Cl₂ is added in 10 minutes. After 10 minutes at −65° C. a solution of 3.2 ml (24.0 mmol) triethylamine in 8 ml CH₂Cl₂ is added in 15 minutes. After 15 more minutes at that temperature the mixture is hydrolysed with 6.0 ml water and warmed up to +20° C. The solution is washed with solutions of KHSO₄ (20%), saturated NaHCO₃ and saturated NaCl. After evaporation the residue is submitted to flash-chromatography (ethyl acetate 25, hexanes 75) to give 2.0 g (77%) of the 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide. ¹H-NMR (300 MHz, CDCl₃): 1.15 (t, 3 H, CH₂CH₃), 2.22 (m, 2 H, CH₂CH₃), 2.87 (t, 2 H, CH₂CH₂), 3.64 (t, 2 H, CH₂CH₂), 3.88 (s, 3 H, OCH₃), 4.72 (m, 2 H, OCH2), 6.77 (m, 2 H, CH arom.), 6.99 (d, 1 H, CH arom.), 7.16 (t, 1 H, NH), 7.57 (d, 8.22, m) and 8.49 (m, 3 H, CH arom.).

e) To a solution of 1.7 g (3.9 mmol) 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide in 32 ml THF, 3.0 g (14.0 mmol) N,N-bis(trimethyl-silyl) methanesulfonamide and 0.1 g (0.32 mmol) tetrabutylammonium bromide (TBAF) are added. The mixture is heated at +70° C. for 7 hours. After cooling, the mixture is diluted with ethyl acetate and washed twice with water. After evaporation of the organic phase the residue is purified by flash-chromatography (ethyl acetate 25, hexanes 75) to give 1.31 g (70%) of the 2-(3,4-dichloro-phenyl)-2-methylthioimino-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide. ¹H-NMR (300 MHz, CDCl₃): 1.15 (t, 3 H, CH₂CH₃), 2.22 (m, 2 H, CH₂CH₃), 2.73 (s, 3 H, SCH₃), 2.83 (t, 2 H, CH₂CH₂) 3.59 (t, 2 H, CH₂CH₂) 3.89 (s, 3 H, OCH₃) 4.73 (m, 2 H, OCH2) 6.78 (m, 2 H, CH arom.), 7.02 (m, 1 H, CH arom.), 7.12 (t, 1 H, NH), 7.30 and 7.58 (m, 3 H, CH arom.).

Example 2 2-{2-[1-(4-Chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-methylthioimino-acetic Acid Methyl Ester

a) 2-{2-[1-(4-Chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-tosyloxyimino-acetic Acid Methyl Ester

To a suspension of 0.96 g sodium hydride (as a 60% dispersion in mineral oil) in 25 ml dimethylformamide 5.78 g (16 mmol) 2-{2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-hydroxyimino-acetic acid methyl ester followed by 3.6 g (19 mmol) p-toluenesulfonyl chloride are added. The mixture is stirred at room temperature during 3 hours and then hydrolysed with ice-water. After extraction with ethyl acetate the organic phase is washed with water and evaporated. The residue is purified by silicagel chromatography (ethyl acetate 1, hexanes 4) yielding 6.2 g (72%) of the 2-{2-[1-(4-chloro-phenyl)-ethylidene-aminooxymethyl]-phenyl}-tosyloxyimino-acetic acid methyl ester. Melting point 124-126° C.

b) To a solution of 2 ml triethylamine in 15 ml chloroform saturated with methanethiol are added 5.15 g (10 mmol) 2-{2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-tosyloxyimino-acetic acid methyl ester. The mixture was stirred at room temperature for 48 hours. After evaporation the residue is purified by silicagel chromatography (ethyl acetate 1, hexanes 5) to give—after elution of 2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-benzonitrile as by-product—1.0 g (28%) of the 2-{2-[1-(4-chloro-phenyl)-ethylideneamino-oxymethyl]-phenyl}-methylthioimino-acetic acid methyl ester. Melting point of 112-113° C.

Example 3 2-{2-[1-(4-Chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-2-methylthioimino-N-methyl-acetamide

0.5 g (1.28 mmol) 2-{2-[1-(4-Chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-methylthioimino-acetic acid methyl ester in 5 ml ethanol containing 33% methylamine are stirred 5.15 at room temperature for 2 hours. After evaporation the residue is crystallized from diethylether to give 435 mg (87%) of the 2-{2-[1-(4-Chloro-phenyl)-ethylideneamino-oxymethyl]-phenyl}-2-methylthioimino-N-methyl-acetamide. Melting point of 118-119° C.

Analogously to the above Examples the following compounds of Tables 1 to 41 may be prepared. In the tables Ph means phenyl.

The geometry of the sulfenimine group of the compounds may be E, Z or a mixture of both.

TABLE 01 Compounds of formula Ia (Ia)

where R is methyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 02:

Compounds of formula Ia where R is ethyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 03:

Compounds of formula Ia where R is propyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 04:

Compounds of formula Ia where R is isopropyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 05:

Compounds of formula Ia where R is n-butyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 06:

Compounds of formula Ia where R is tert-butyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 07:

Compounds of formula Ia where R is 3-chloropropyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 08:

Compounds of the formula Ia where R is 2-methyl-2-propyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 09:

Compounds of formula Ia where R is allyl and wherein the combination of A, B and E corresponds to one line in Table A.

Table 10:

Compounds of formula Ia where R is CF₃ and wherein the combination of A, B and E corresponds to one line in Table A.

TABLE 11 Compounds of formula Ib (Ib)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 12 Compounds of the formula Ic (Ic)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 13 Compounds of the formula Id (Id)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 14 Compounds of the formula Ie (Ie)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 15 Compounds of the formula If (If)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 16 Compounds of the formula Ig (Ig)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 17 Compounds of the formula Ih (Ih)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 18 Compounds of the formula Ii (Ii)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 19 Compounds of the formula Ij (Ij)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 20 Compounds of the formula Ik (Ik)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 21 Compounds of the formula Il (Il)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 22 Compounds of the formula Im (Im)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 23 Compounds of the formula In (In)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 24 Compounds of the formula Io (Io)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 25 Compounds of the formula Ip

(Ip)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 26 Compounds of the formula Iq

(Iq)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 27 Compounds of the formula Ir

(Ir)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 28 Compounds of the formula Is

(Is)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 29 Compounds of the formula It

(It)

wherein the combination of R, A and B corresponds to one line in Table B.

TABLE 30 Compounds of the formula Iu

(Iu)

wherein the combination of W and Z corresponds to one line in Table C.

TABLE 31 Compounds of the formula Iv

(Iv)

wherein the combination of W and Z corresponds to one line in Table C.

TABLE 32 Compounds of the formula XIa

(XIa)

where -B-E is O-methyl and wherein the combination of A and R corresponds to one line in Table D.

Table 33:

Compounds of formula XIa where -B-E is O-ethyl and wherein the combination of A and R corresponds to one line in Table D.

Table 34:

Compounds of formula XIa where Y is O-n-propyl and wherein the combination of A and R corresponds to one line in Table D.

Table 35:

Compounds of formula XIa where -B-E is O-iso-propyl and wherein the combination of A and By R corresponds to one line in Table D.

Table 36:

Compounds of formula XIa where -B-E is O-n-butyl and wherein the combination of A and R corresponds to one line in Table D.

Table 37:

Compounds of formula XIa where -B-E is O-sec-butyl and wherein the combination of A and R corresponds to one line in Table D.

Table 38:

Compounds of formula XIa where -B-E is O-tert-butyl and wherein the combination of A and R corresponds to one line in Table D.

Table 39:

Compounds of formula XIa where -B-E is O-phenyl and wherein the combination of A and R corresponds to one line in Table D.

Table 40:

Compounds of formula XIa where -B-E is O-benzyl and wherein the combination of A and R corresponds to one line in Table D.

TABLE A A B E 001 Ph CH₂ Ph 002 Ph CH₂ 4-Cl—Ph 003 Ph CH₂ 3,4-di—Cl—Ph 004 Ph CH₂ 2,4-di—Cl—Ph 005 Ph CH₂ 4-Br—Ph 006 Ph CH₂ 4-CH₃—Ph 007 Ph CH₂ 4-C₂H₅—Ph 008 Ph CH₂ 4-OCH₃—Ph 009 Ph CH₂ 4-CF₃—Ph 010 Ph CH₂ 4-cycl-C₅H₁₁—Ph 011 Ph CH₂ 3-OCH₃-4-OPh—Ph 012 Ph CH₂ 3-OCH₃-4-SCH₃—Ph 013 Ph CH₂ 4-CH₃OOC—Ph 014 Ph CH₂ 3-NO₂—Ph 015 Ph CH₂ 4-CN—Ph 016 Ph CH₂ 4-(CH₃)₂N—Ph 017 Ph CH(CH₃) Ph 018 Ph CH(CH₃) 4-Cl—Ph 019 Ph CH(CH₃) 3,4-di—Cl—Ph 020 Ph CH(CH₃) 2,4-di—Cl—Ph 021 Ph CH(CH₃) 4-Br—Ph 022 Ph CH(CH₃) 4-CH₃—Ph 023 Ph CH(CH₃) 4-C₂H₅—Ph 024 Ph CH(CH₃) 4-OCH₃—Ph 025 Ph CH(CH₃) 4-CF₃—Ph 026 Ph CH(CH₃) 4-cycl-C₅H₁₁—Ph 027 Ph CH(CH₃) 3-OCH₃-4-OPh—Ph 028 Ph CH(CH₃) 3-OCH₃-4-SCH₃—Ph 029 Ph CH(CH₃) 4-CH₃OOC—Ph 030 Ph CH(CH₃) 3-NO₂—Ph 031 Ph CH(CH₃) 4-Cl—Ph 032 Ph CH(CH₃) 4-(CH₃)₂N—Ph 033 Ph CH₂—CH₂ Ph 034 Ph CH₂—CH₂ 4-Cl—Ph 035 Ph CH₂—CH₂ 3,4-di—Cl—Ph 036 Ph CH₂—CH₂ 2,4-di—Cl—Ph 037 Ph CH₂—CH₂ 4-Br—Ph 038 Ph CH₂—CH₂ 4-CH₃—Ph 039 Ph CH₂—CH₂ 4-C₂H₅—Ph 040 Ph CH₂—CH₂ 4-OCH₃—Ph 041 Ph CH₂—CH₂ 4-CF₃—Ph 042 Ph CH₂—CH₂ 4-cycl-C₅H₁₁—Ph 043 Ph CH₂—CH₂ 3-OCH₃-4-OPh—Ph 044 Ph CH₂—CH₂ 3-OCH₃-4-SCH₃—Ph 045 Ph CH₂—CH₂ 4-CH₃OOC—Ph 046 Ph CH₂—CH₂ 3-NO₂—Ph 047 Ph CH₂—CH₂ 4-CN—Ph 048 Ph CH₂—CH₂ 4-(CH₃)₂N—Ph 049 Ph CH(CH₃)—CH₂ Ph 050 Ph CH(CH₃)—CH₂ 4-Cl—Ph 051 Ph CH(CH₃)—CH₂ 3,4-di-Cl—Ph 052 Ph CH(CH₃)—CH₂ 2,4-di-Cl—Ph 053 Ph CH(CH₃)—CH₂ 4-Br—Ph 054 Ph CH(CH₃)—CH₂ 4-CH₃—Ph 055 Ph CH(CH₃)—CH₂ 4-C₂H₅—Ph 056 Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 057 Ph CH(CH₃)—CH₂ 4-CF₃—Ph 058 Ph CH(CH₃)—CH₂ 4 cycl-C₅H₁₁—Ph 059 Ph CH(CH₃)—CH₂ 3-OCH₃-4-OPh—Ph 060 Ph CH(CH₃)—CH₂ 3-OCH₃-4-SCH₃—Ph 061 Ph CH(CH₃)—CH₂ 4-CH₃OOC—Ph 062 Ph CH(CH₃)—CH₂ 3-NO₂—Ph 063 Ph CH(CH₃)—CH₂ 4-CN—Ph 064 Ph CH(CH₃)—CH₂ 4-(CH₃)₂N—Ph 065 4-Cl—Ph CH₂ Ph 066 4-Cl—Ph CH₂ 4-Cl—Ph 067 4-Cl—Ph CH₂ 3,4-di—Cl—Ph 068 4-Cl—Ph CH₂ 2,4-di—Cl—Ph 069 4-Cl—Ph CH₂ 4-Br—Ph 070 4-Cl—Ph CH₂ 4-CH₃—Ph 071 4-Cl—Ph CH₂ 4-C₂H₅—Ph 072 4-Cl—Ph CH₂ 4-OCH₃—Ph 073 4-Cl—Ph CH₂ 4-CF₃—Ph 074 4-Cl—Ph CH₂ 4-cycl-C₅H₁₁—Ph 075 4-Cl—Ph CH₂ 3-OCH₃-4-OPh—Ph 076 4-Cl—Ph CH₂ 3-OCH₃-4-SCH₃—Ph 077 4-Cl—Ph CH₂ 4-CH₃OOC—Ph 078 4-Cl—Ph CH₂ 3-NO₂—Ph 079 4-Cl—Ph CH₂ 4-CN—Ph 080 4-Cl—Ph CH₂ 4-(CH₃)₂N—Ph 081 4-Cl—Ph CH(CH₃) Ph 082 4-Cl—Ph CH(CH₃) 4-Cl—Ph 083 4-Cl—Ph CH(CH₃) 3,4-di—Cl—Ph 084 4-Cl—Ph CH(CH₃) 2,4-di—Cl—Ph 085 4-Cl—Ph CH(CH₃) 4-Br—Ph 086 4-Cl—Ph CH(CH₃) 4-CH₃—Ph 087 4-Cl—Ph CH(CH₃) 4-C₂H₅—Ph 088 4-Cl—Ph CH(CH₃) 4-OCH₃—Ph 089 4-Cl—Ph CH(CH₃) 4-CF₃—Ph 090 4-Cl—Ph CH(CH₃) 4-cycl-C₅H₁₁—Ph 091 4-Cl—Ph CH(CH₃) 3-OCH₃-4-OPh—Ph 092 4-Cl—Ph CH(CH₃) 3-OCH₃-4-SCH₃—Ph 093 4-Cl—Ph CH(CH₃) 4-CH₃OOC—Ph 094 4-Cl—Ph CH(CH₃) 3-NO₂—Ph 095 4-Cl—Ph CH(CH₃) 4-CN—Ph 096 4-Cl—Ph CH(CH₃) 4-(CH₃)₂N—Ph 097 4-Cl—Ph CH₂—CH₂ Ph 098 4-Cl—Ph CH₂—CH₂ 4-Cl—Ph 099 4-Cl—Ph CH₂—CH₂ 3,4-di—Cl—Ph 100 4-Cl—Ph CH₂—CH₂ 2,4-di—Cl—Ph 101 4-Cl—Ph CH₂—CH₂ 4-Br—Ph 102 4-Cl—Ph CH₂—CH₂ 4-CH₃—Ph 103 4-Cl—Ph CH₂—CH₂ 4-C₂H₅—Ph 104 4-Cl—Ph CH₂—CH₂ 4-OCH₃—Ph 105 4-Cl—Ph CH₂—CH₂ 4-CF₃—Ph 106 4-Cl—Ph CH₂—CH₂ 4-cycl-C₅H₁₁—Ph 107 4-Cl—Ph CH₂—CH₂ 3-OCH₃-4-OPh—Ph 108 4-Cl—Ph CH₂—CH₂ 3-OCH₃-4-SCH₃—Ph 109 4-Cl—Ph CH₂—CH₂ 4-CH₃OOC—Ph 110 4-Cl—Ph CH₂—CH₂ 3-NO₂—Ph 111 4-Cl—Ph CH₂—CH₂ 4-CN—Ph 112 4-Cl—Ph CH₂—CH₂ 4-(CH₃)₂N—Ph 113 4-Cl—Ph CH(CH₃)—CH₂ Ph 114 4-Cl—Ph CH(CH₃)—CH₂ 4-Cl—Ph 115 4-Cl—Ph CH(CH₃)—CH₂ 3,4-di—Cl—Ph 116 4-Cl—Ph CH(CH₃)—CH₂ 2,4-di—Cl—Ph 117 4-Cl—Ph CH(CH₃)—CH₂ 4-Br—Ph 118 4-Cl—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 119 4-Cl—Ph CH(CH₃)—CH₂ 4-C₂H₅—Ph 120 4-Cl—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 121 4-Cl—Ph CH(CH₃)—CH₂ 4-CF₃—Ph 122 4-Cl—Ph CH(CH₃)—CH₂ 4-cycl-C₅H₁₁—Ph 123 4-Cl—Ph CH(CH₃)—CH₂ 3-OCH₃-4-OPh—Ph 124 4-Cl—Ph CH(CH₃)—CH₂ 3-OCH₃-4-SCH₃—Ph 125 4-Cl—Ph CH(CH₃)—CH₂ 4-CH₃OOC—Ph 126 4-Cl—Ph CH(CH₃)—CH₂ 3-NO₂—Ph 127 4-Cl—Ph CH(CH₃)—CH₂ 4-CN—Ph 128 4-Cl—Ph CH(CH₃)—CH₂ 4-CH₃)₂N—Ph 129 3,4-di—Cl—Ph CH₂ Ph 130 3,4-di—Cl—Ph CH₂ 4-Cl—Ph 131 3,4-di—Cl—Ph CH₂ 3,4-di—Cl—Ph 132 3,4-di—Cl—Ph CH₂ 2,4-di—Cl—Ph 133 3,4-di—Cl—Ph CH₂ 4-Br—Ph 134 3,4-di—Cl—Ph CH₂ 4-CH₃—Ph 135 3,4-di—Cl—Ph CH₂ 4-C₂H₅—Ph 136 3,4-di—Cl—Ph CH₂ 4-OCH₃—Ph 137 3,4-di—Cl—Ph CH₂ 4-CF₃—Ph 138 3,4-di—Cl—Ph CH₂ 4-cycl-C₅H₁₁—Ph 139 3,4-di—Cl—Ph CH₂ 3-OCH₃-4-OPh—Ph 140 3,4-di—Cl—Ph CH₂ 3-OCH₃-4-SCH₃—Ph 141 3,4-di—Cl—Ph CH₂ 4-CH₃OOC—Ph 142 3,4-di—Cl—Ph CH₂ 3-NO₂—Ph 143 3,4-di—Cl—Ph CH₂ 4-CN—Ph 144 3,4-di—Cl—Ph CH₂ 4-(CH₃)₂N—Ph 145 3,4-di—Cl—Ph CH(CH₃) Ph 146 3,4-di—Cl—Ph CH(CH₃) 4-Cl—Ph 147 3,4-di—Cl—Ph CH(CH₃) 3,4-di—Cl—Ph 148 3,4-di—Cl—Ph CH(CH₃) 2,4-di—Cl—Ph 149 3,4-di—Cl—Ph CH(CH₃) 4-Br—Ph 150 3,4 di—Cl—Ph CH(CH₃) 4-CH₃—Ph 151 3,4-di—Cl—Ph CH(CH₃) 4-C₂H₅—Ph 152 3,4-di—Cl—Ph CH(CH₃) 4-OCH₃—Ph 153 3,4-di—Cl—Ph CH(CH₃) 4-CF₃—Ph 154 3,4-di—Cl—Ph CH(CH₃) 4-cycl-C₅H₁₁—Ph 155 3,4-di—Cl—Ph CH(CH₃) 3-OCH₃-4-OPh—Ph 156 3,4-di—Cl—Ph CH(CH₃) 3-OCH₃-4-SCH₃—Ph 157 3,4-di—Cl—Ph CH(CH₃) 4-CH₃OOC—Ph 158 3,4-di—Cl—Ph CH(CH₃) 3-NO₂—Ph 159 3,4-di—Cl—Ph CH(CH₃) 4-CN—Ph 160 3,4-di—Cl—Ph CH(CH₃) 4-(CH₃)₂N—Ph 161 3,4-di—Cl—Ph CH₂—CH₂ Ph 162 3,4-di—Cl—Ph CH₂—CH₂ 4-Cl—Ph 163 3,4-di—Cl—Ph CH₂—CH₂ 3,4-di—Cl—Ph 164 3,4-di—Cl—Ph CH₂—CH₂ 2,4-di—Cl—Ph 165 3,4-di—Cl—Ph CH₂—CH₂ 4-Br—Ph 166 3,4-di—Cl—Ph CH₂—CH₂ 4-CH₃—Ph 167 3,4-di—Cl—Ph CH₂—CH₂ 4-C₂H₅—Ph 168 3,4-di—Cl—Ph CH₂—CH₂ 4-OCH₃—Ph 169 3,4-di—Cl—Ph CH₂—CH₂ 4-CF₃—Ph 170 3,4-di—Cl—Ph CH₂—CH₂ 4-cycl-C₅H₁₁—Ph 171 3,4-di—Cl—Ph CH₂—CH₂ 3-OCH₃-4-OPh—Ph 172 3,4-di—Cl—Ph CH₂—CH₂ 3-OCH₃-4-SCH₃—Ph 173 3,4-di—Cl—Ph CH₂—CH₂ 4-CH₃OOC—Ph 174 3,4-di—Cl—Ph CH₂—CH₂ 3-NO₂—Ph 175 3,4-di—Cl—Ph CH₂—CH₂ 4-CN—Ph 176 3,4-di—Cl—Ph CH₂—CH₂ 4-(CH₃)₂N—Ph 177 3,4-di—Cl—Ph CH(CH₃)—CH₂ Ph 178 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-Cl—Ph 179 3,4-di—Cl—Ph CH(CH₃)—CH₂ 3,4-di—Cl—Ph 180 3,4-di—Cl—Ph CH(CH₃)—CH₂ 2,4-di—Cl—Ph 181 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-Br—Ph 182 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 183 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-C₂H₅—Ph 184 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 185 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-CF₃—Ph 186 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-cycl-C₅H₁₁—Ph 187 3,4-di—Cl—Ph CH(CH₃)—CH₂ 3-OCH₃-4-OPh—Ph 188 3,4-di—Cl—Ph CH(CH₃)—CH₂ 3-OCH₃-4-SCH₃—Ph 189 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-CH₃OOC—Ph 190 3,4-di—Cl—Ph CH(CH₃)—CH₂ 3-NO₂—Ph 191 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-CN—Ph 192 3,4-di—Cl—Ph CH(CH₃)—CH₂ 4-(CH₃)₂N—Ph 193 4-Br—Ph CH₂—CH₂ Ph 194 4-Br—Ph CH₂—CH₂ 4-Cl—Ph 195 4-Br—Ph CH₂—CH₂ 4-CH₃—Ph 196 4-Br—Ph CH₂—CH₂ 4-C₂H_(5—Ph) 197 4-Br—Ph CH₂—CH₂ 4-OCH₃—Ph 198 4-Br—Ph CH₂—CH₂ 3-OCH₃-4-OPh—Ph 199 4-Br—Ph CH₂—CH₂ 3-OCH₃-4-SCH₃—Ph 200 4-Br—Ph CH(CH₃)—CH₂ Ph 201 4-Br—Ph CH(CH₃)—CH₂ 4-Cl—Ph 202 4-Br—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 203 4-Br—Ph CH(CH₃)—CH₂ 4-C₂H₅—Ph 204 4-Br—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 205 4-Br—Ph CH(CH₃)—CH₂ 3-OCH₃-4-OPh—Ph 206 4-Br—Ph CH(CH₃)—CH₂ 3-OCH₃-4-SCH₃—Ph 207 4-OCH₃—Ph CH₂—CH₂ Ph 208 4-OCH₃—Ph CH₂—CH₂ 4-Cl—Ph 209 4-OCH₃—Ph CH₂—CH₂ 4-CH₃—Ph 210 4-OCH₃—Ph CH₂—CH₂ 4-C₂H₅—Ph 211 4-OCH₃—Ph CH₂—CH₂ 4-OCH 3—Ph 212 4-OCH₃—Ph CH₂—CH₂ 3-OCH₃-4-OPh—Ph 213 4-OCH₃—Ph CH₂—CH₂ 3-OCH₃-4-SCH₃—Ph 214 4-OCH₃—Ph CH(CH₃)—CH₂ Ph 215 4-OCH₃—Ph CH(CH₃)—CH₂ 4-Cl—Ph 216 4-OCH₃—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 217 4-OCH₃—Ph CH(CH₃)—CH₂ 4-C₂H₅—Ph 218 4-OCH₃—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 219 4-OCH₃—Ph CH(CH₃)—CH₂ 3-OCH₃-4-OPh—Ph 220 4-OCH₃—Ph CH(CH₃)—CH₂ 3-OCH₃4-SCH₃—Ph 221 4-CH₃—Ph CH₂—CH₂ Ph 222 4-CH₃—Ph CH₂—CH₂ 4-Cl-Ph 223 4-CH₃—Ph CH₂—CH₂ 4 CH₃—Ph 224 4-CH₃—Ph CH₂—CH₂ 4-C₂H₅—Ph 225 4-CH₃—Ph CH₂—CH₂ 4-OCH₃—Ph 226 4-CH₃—Ph CH₂—CH₂ 3-OCH₃-4-OPh—Ph 227 4-CH₃—Ph CH₂—CH₂ 3-OCH₃-4-SCH₃—Ph 228 4-CH₃—Ph CH(CH₃)—CH₂ Ph 229 4-CH₃—Ph CH(CH₃)—CH₂ 4-Cl—Ph 230 4-CH₃—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 231 4-CH₃—Ph CH(CH₃)—CH₂ 4-C₂H₅—Ph 232 4-CH₃—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 233 4-CH₃—Ph CH(CH₃)—CH₂ 3-OCH₃-4-OPh—Ph 234 4-CH₃—Ph CH(CH₃)—CH₂ 3-OCH₃-4-SCH₃—Ph 235 4-F—Ph CH₂—CH₂ 4-Cl—Ph 236 4-F—Ph CH₂—CH₂ 4-CH₃—Ph 237 4-F—Ph CH₂—CH₂ 4-OCH₃—Ph 238 4-F—Ph CH(CH₃)—CH₂ 4-Cl—Ph 239 4-F—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 240 4-F—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 241 3,4-OCH₂O—Ph CH(CH₃)—CH₂ 4-Cl—Ph 242 3,4-OCH₂O—Ph CH₂—Ch₂ 4-CH₃—Ph 243 3,4-OCH₂O—Ph CH₂—CH₂ 4-OCH₃—Ph 244 3,4-OCH₂O—Ph CH(CH₃)—CH₂ 4-Cl—Ph 245 3,4-OCH₂O—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 246 3,4-OCH₂O Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 247 3,4-di-OCH₃—Ph CH₂—CH₂ 4-Cl—Ph 248 3,4-di-OCH₃—Ph CH₂—CH₂ 4-CH₃—Ph 249 3,4-di-OCH₃—Ph CH₂—CH₂ 4-OCH₃—Ph 250 3,4-di-OCH₃—Ph CH(CH₃)—CH₂ 4-Cl—Ph 251 3,4-di-OCH₃—Ph CH(CH₃—CH₂ 4-CH₃—Ph 252 3,4-di-OCH₃—Ph CH(CH₃—CH₂ 4-OCH₃—Ph 253 3,4-di-CH₃—Ph CH₂—CH₂ 4-Cl—Ph 254 3,4-di-CH₃—Ph CH₂—CH₂ 4-CH₃—Ph 255 3,4-di-CH₃—Ph CH₂—CH₂ 4-OCH₃—Ph 256 3,4-di-CH₃—Ph CH(CH₃)—CH₂ 4-Cl—Ph 257 3,4-di-CH₃—Ph CH(CH₃)—CH₂ 4-CH₃—Ph 258 3,4-di-CH₃—Ph CH(CH₃)—CH₂ 4-OCH₃—Ph 259 3,4-di-Cl—Ph CH₂CH₂CH₂ 3,4-di-OCH₃—Ph 260 3,4-di-Cl—Ph CH₂—CH₂ 3-OCH₃-4-OC₁₂H₂₅—Ph

TABLE B R A B 001 CH₃ 4-Cl—Ph CH₂CH₂ 002 C₂H₅ 4-Cl—Ph CH₂CH₂ 003 C₃H₇-n 4-Cl—Ph CH₂CH₂ 004 C₃H₇-i 4-Cl—Ph CH₂CH₂ 005 C₄H₉-n 4-Cl—Ph CH₂CH₂ 006 CH₃ 4-Cl—Ph CH(CH₃)CH₂ 007 C₂H₅ 4-Cl—Ph CH(CH₃)CH₂ 008 C₃H₇-n 4-Cl—Ph CH(CH₃)CH₂ 009 C₃H₇-i 4-Cl—Ph CH(CH₃)CH₂ 010 C₄H₉-n 4-Cl—Ph CH(CH₃)CH₂ 011 CH₃ 3,4-di-Cl—Ph CH₂CH₂ 012 C₂H₅ 3,4-di-Cl—Ph CH₂CH₂ 013 C₃H₇-n 3,4-di-Cl—Ph CH₂CH₂ 014 C₃H₇-i 3,4-di-Cl—Ph CH₂CH₂ 015 C₄H₉-n 3,4-di-Cl—Ph CH₂CH₂ 016 CH₃ 3,4-di-Cl—Ph CH(CH₃)CH₂ 017 C₂H₅ 3,4-di-Cl—Ph CH(CH₃)CH₂ 018 C₃H₇-n 3,4-di-Cl—Ph CH(CH₃)CH₂ 019 C₃H₇-i 3,4-di-Cl—Ph CH(CH₃)CH₂ 020 C₄H₉-n 3,4-di-Cl—Ph CH(CH₃)CH₂ 021 CH₃ Ph CH₂CH₂ 022 C₂H₅ Ph CH₂CH₂ 023 C₃H₇-n Ph CH₂CH₂ 024 C₃H₇-i Ph CH₂CH₂ 025 C₄H₉-n Ph CH₂CH₂ 026 CH₃ Ph CH(CH₃)CH₂ 027 C₂H₅ Ph CH(CH₃)CH₂ 028 C₃H₇-n Ph CH(CH₃)CH₂ 029 C₃H₇-i Ph CH(CH₃)CH₂ 030 C₄H₉-n Ph CH(CH₃)CH₂ 031 CH₃ 4-Br—Ph CH₂CH₂ 032 C₂H₅ 4-Br—Ph CH₂CH₂ 033 C₃H₇-n 4-Br—Ph CH₂CH₂ 034 C₃H₇-i 4-Br—Ph CH₂CH₂ 035 C₄H₉-n 4-Br—Ph CH₂CH₂ 036 CH₃ 4-Br—Ph CH(CH₃)CH₂ 037 C₂H₅ 4-Br—Ph CH(CH₃)CH₂ 038 C₃H₇-n 4-Br—Ph CH(CH₃)CH₂ 039 C₃H₇-i 4-Br—Ph CH(CH₃)CH₂ 040 C₄H₉-n 4-Br—Ph CH(CH₃)CH₂ 041 CH₃ 4-CH₃—Ph CH₂CH₂ 042 C₂H₅ 4-CH₃—Ph CH₂CH₂ 043 C₃H₇-n 4-CH₃—Ph CH₂CH₂ 044 C₃H₇-i 4-CH₃—Ph CH₂CH₂ 045 C₄H₉-n 4-CH₃—Ph CH₂CH₂ 046 CH₃ 4-CH₃—Ph CH(CH₃)CH₂ 047 C₂H₅ 4-CH₃—Ph CH(CH₃)CH₂ 048 C₃H₇-n 4-CH₃—Ph CH(CH₃)CH₂ 049 C₃H₇-i 4-CH₃—Ph CH(CH₃)CH₂ 050 C₄H₉-n 4-CH₃—Ph CH(CH₃)CH₂ 051 CH₃ 4-CH₃O—Ph CH₂CH₂ 052 C₂H₅ 4-CH₃O—Ph CH₂CH₂ 053 C₃H₇-n 4-CH₃O—Ph CH₂CH₂ 054 C₃H₇-i 4-CH₃O—Ph CH₂CH₂ 055 C₄H₉-n 4-CH₃O—Ph CH₂CH₂ 056 CH₃ 4-CH₃O—Ph CH(CH₃)CH₂ 057 C₂H₅ 4-CH₃O—Ph CH(CH₃)CH₂ 058 C₃H₇-n 4-CH₃O—Ph CH(CH₃)CH₂ 059 C₃H₇-i 4-CH₃O—Ph CH(CH₃)CH₂ 060 C₄H₉-n 4-CH₃O—Ph CH(CH₃)CH₂ 061 CH₃ 4-CF₃—Ph CH₂CH₂ 062 C₂H₅ 4-CF₃—Ph CH₂CH₂ 063 C₃H₇-n 4-CF₃—Ph CH₂CH₂ 064 C₃H₇-i 4-CF₃—Ph CH₂CH₂ 065 C₄H₉-n 4-CF₃—Ph CH₂CH₂ 066 CH₃ 4-CF₃—Ph CH(CH₃)CH₂ 067 C₂H₅ 4-CF₃—Ph CH(CH₃)CH₂ 068 C₃H₇-n 4-CF₃—Ph CH(CH₃)CH₂ 069 C₃H₇-i 4-CF₃—Ph CH(CH₃)CH₂ 070 C₄H₉-n 4-CF₃—Ph CH(CH₃)CH₂ 071 CH₃ 4-F—Ph CH₂CH₂ 072 C₂H₅ 4-F—Ph CH₂CH₂ 073 C₃H₇-n 4-F—Ph CH₂CH₂ 074 C₃H₇-i 4-F—Ph CH₂CH₂ 075 C₄H₉-n 4-F—Ph CH₂CH₂ 076 CH₃ 4-F—Ph CH(CH₃)CH₂ 077 C₂H₅ 4-F—Ph CH(CH₃)CH₂ 078 C₃H₇-n 4-F—Ph CH(CH₃)CH₂ 079 C₃H₇-i 4-F—Ph CH(CH₃)CH₂ 080 C₄H₉-n 4-F—Ph CH(CH₃)CH₂ 081 CH₃ 4-CF₃O—Ph CH₂CH₂ 082 C₂H₅ 4-CF₃O—Ph CH₂CH₂ 083 C₃H₇-n 4-CF₃O—Ph CH₂CH₂ 084 C₃H₇-i 4-CF₃O—Ph CH₂CH₂ 085 C₄H₉-n 4-CF₃O—Ph CH₂CH₂ 086 CH₃ 4-CF₃O—Ph CH(CH₃)CH₂ 087 C₂H₅ 4-CF₃O—Ph CH(CH₃)CH₂ 088 C₃H₇-n 4-CF₃O—Ph CH(CH₃)CH₂ 089 C₃H₇-i 4-CF₃O—Ph CH(CH₃)CH₂ 090 C₄H₉-n 4-CF₃O—Ph CH(CH₃)CH₂ 091 CH₃ 3,4-di-OCH₃—Ph CH₂CH₂ 092 C₂H₅ 3,4-di-OCH₃—Ph CH₂CH₂ 093 C₃H₇-n 3,4-di-OCH₃—Ph CH₂CH₂ 094 C₃H₇-i 3,4-di-OCH₃—Ph CH₂CH₂ 095 C₄H₉-n 3,4-di-OCH₃—Ph CH₂CH₂ 096 CH₃ 3,4-di-OCH₃—Ph CH(CH₃)CH₂ 097 C₂H₅ 3,4-di-OCH₃—Ph CH(CH₃)CH₂ 098 C₃H₇-n 3,4-di-OCH₃—Ph CH(CH₃)CH₂ 099 C₃H₇-i 3,4-di-OCH₃—Ph CH(CH₃)CH₂ 100 C₄H₉-n 3,4-di-OCH₃—Ph CH(CH₃)CH₂ 101 CH₃ 3,4-OCH₂—O—Ph CH₂CH₂ 102 C₂H₅ 3,4-OCH₂—O—Ph CH₂CH₂ 103 C₃H₇-n 3,4-OCH₂—O—Ph CH₂CH₂ 104 C₃H₇-i 3,4-OCH₂—O—Ph CH₂CH₂ 105 C₄H₉-n 3,4-OCH₂—O—Ph CH₂CH₂ 106 CH₃ 3,4-OCH₂—O—Ph CH(CH₃)CH₂ 107 C₂H₅ 3,4-OCH₂—O—Ph CH(CH₃)CH₂ 108 C₃H₇-n 3,4-OCH₂—O—Ph CH(CH₃)CH₂ 109 C₃H₇-i 3,4-OCH₂—O—Ph CH(CH₃)CH₂ 110 C₄H₉-n 3,4-OCH₂—O—Ph CH(CH₃)CH₂ 111 CH₃ 3,4-di-F—Ph CH₂CH₂ 112 C₂H₅ 3,4-di-F—Ph CH₂CH₂ 113 C₃H₇-n 3,4-di-F—Ph CH₂CH₂ 114 C₃H₇-i 3,4-di-F—Ph CH₂CH₂ 115 C₄H₉-n 3,4-di-F—Ph CH₂CH₂ 116 CH₃ 3,4-di-F—Ph CH(CH₃)CH₂ 117 C₂H₅ 3,4-di-F—Ph CH(CH₃)CH₂ 118 C₃H₇-n 3,4-di-F—Ph CH(CH₃)CH₂ 119 C₃H₇-i 3,4-di-F—Ph CH(CH₃)CH₂ 120 C₄H₉-n 3,4-di-F—Ph CH(CH₃)CH₂ 121 CH₃

CH₂CH₂ 122 C₂H₅

CH₂CH₂ 123 C₃H₇-n

CH₂CH₂ 124 C₃H₇-i

CH₂CH₂ 125 C₄H₉-n

CH₂CH₂ 126 CH₃

CH(CH₃)CH₂ 127 C₂H₅

CH(CH₃)CH₂ 128 C₃H₇-n

CH(CH₃)CH₂ 129 C₃H₇-i

CH(CH₃)CH₂ 130 C₄H₉-n

CH(CH₃)CH₂ 131 CH₃

CH₂CH₂ 132 C₂H₅

CH₂CH₂ 133 C₃H₇-n

CH₂CH₂ 134 C₃H₇-i

CH₂CH₂ 135 C₄H₉-n

CH₂CH₂ 136 CH₃

CH(CH₃)CH₂ 137 C₂H₅

CH(CH₃)CH₂ 138 C₃H₇-n

CH(CH₃)CH₂ 139 C₃H₇-i

CH(CH₃)CH₂ 140 C₄H₉-n

CH(CH₃)CH₂ 141 CH₃

CH₂CH₂ 142 C₂H₅

CH₂CH₂ 143 C₃H₇-n

CH₂CH₂ 144 C₃H₇-i

CH₂CH₂ 145 C₄H₉-n

CH₂CH₂ 146 CH₃

CH(CH₃)CH₂ 147 C₂H₅

CH(CH₃)CH₂ 148 C₃H₇-n

CH(CH₃)CH₂ 149 C₃H₇-i

CH(CH₃)CH₂ 150 C₄H₉-n

CH(CH₃)CH₂ 151 CH₃ 4-Ph—Ph CH₂CH₂ 152 C₂H₅ 4-Ph—Ph CH₂CH₂ 153 C₃H₇-n 4-Ph—Ph CH₂CH₂ 154 C₃H₇-i 4-Ph—Ph CH₂CH₂ 155 C₄H₉-n 4-Ph—Ph CH₂CH₂ 156 CH₃ 4-Ph—Ph CH(CH₃)CH₂ 157 C₂H₅ 4-Ph—Ph CH(CH₃)CH₂ 158 C₃H₇-n 4-Ph—Ph CH(CH₃)CH₂ 159 C₃H₇-i 4-Ph—Ph CH(CH₃)CH₂ 160 C₄H₉-n 4-Ph—Ph CH(CH₃)CH₂ 161 CH₃ 4′-Cl—Ph-4-Ph CH₂CH₂ 162 C₂H₅ 4′-Cl—Ph-4-Ph CH₂CH₂ 163 C₃H₇-n 4′-Cl—Ph-4-Ph CH₂CH₂ 164 C₃H₇-i 4′-Cl—Ph-4-Ph CH₂CH₂ 165 C₄H₉-n 4′-Cl—Ph-4-Ph CH₂CH₂ 166 CH₃ 4′-Cl—Ph-4-Ph CH(CH₃)CH₂ 167 C₂H₅ 4′-Cl—Ph-4-Ph CH(CH₃)CH₂ 168 C₃H₇-n 4′-Cl—Ph-4-Ph CH(CH₃)CH₂ 169 C₃H₇-i 4′-Cl—Ph-4-Ph CH(CH₃)CH₂ 170 C₄H₉-n 4′-Cl—Ph-4-Ph CH(CH₃)CH₂ 171 CH₃ 4′-CH₃—Ph-4-Ph CH₂CH₂ 172 C₂H₅ 4′-CH₃—Ph-4-Ph CH₂CH₂ 173 C₃H₇-n 4′-CH₃—Ph-4-Ph CH₂CH₂ 174 C₃H₇-i 4′-CH₃—Ph-4-Ph CH₂CH₂ 175 C₄H₉-n 4′-CH₃—Ph-4-Ph CH₂CH₂ 176 CH₃ 4′-CH₃—Ph-4-Ph CH(CH₃)CH₂ 177 C₂H₅ 4′-CH₃—Ph-4-Ph CH(CH₃)CH₂ 178 C₃H₇-n 4′-CH₃—Ph-4-Ph CH(CH₃)CH₂ 179 C₃H₇-i 4′-CH₃—Ph-4-Ph CH(CH₃)CH₂ 180 C₄H₉-n 4′-CH₃—Ph-4-Ph CH(CH₃)CH₂ 181 CH₃ 3,4-di-CH₃—Ph CH₂CH₂ 182 C₂H₅ 3,4-di-CH₃—Ph CH₂CH₂ 183 C₃H₇-n 3,4-di-CH₃—Ph CH₂CH₂ 184 C₃H₇-i 3,4-di-CH₃—Ph CH₂CH₂ 185 C₄H₉-n 3,4-di-CH₃—Ph CH₂CH₂ 186 CH₃ 3,4-di-CH₃—Ph CH(CH₃)CH₂ 187 C₂H₅ 3,4-di-CH₃—Ph CH(CH₃)CH₂ 188 C₃H₇-n 3,4-di-CH₃—Ph CH(CH₃)CH₂ 189 C₃H₇-i 3,4-di-CH₃—Ph CH(CH₃)CH₂ 190 C₄H₉-n 3,4-di-CH₃—Ph CH(CH₃)CH₂ 191 CH₃ 4-cycl-C₆H₁₁—Ph CH₂CH₂ 192 C₂H₅ 4-cycl-C₆H₁₁—Ph CH₂CH₂ 193 C₃H₇-n 4-cycl-C₆H₁₁—Ph CH₂CH₂ 194 C₃H₇-i 4-cycl-C₆H₁₁—Ph CH₂CH₂ 195 C₄H₉-n 4-cycl-C₆H₁₁—Ph CH₂CH₂ 196 CH₃ 4-cycl-C₆H₁₁—Ph CH(CH₃)CH₂ 197 C₂H₅ 4-cycl-C₆H₁₁—Ph CH(CH₃)CH₂ 198 C₃H₇-n 4-cycl-C₆H₁₁—Ph CH(CH₃)CH₂ 199 C₃H₇-i 4-cycl-C₆H₁₁—Ph CH(CH₃)CH₂ 200 C₄H₉-n 4-cycl-C₆H₁₁—Ph CH(CH₃)CH₂ 201 CH₃ 4-[N(CH₃)₂]—Ph CH₂CH₂ 202 C₂H₅ 4-[N(CH₃)₂]—Ph CH₂CH₂ 203 C₃H₇-n 4-[N(CH₃)₂]—Ph CH₂CH₂ 204 C₃H₇-i 4-[N(CH₃)₂]—Ph CH₂CH₂ 205 C₄H₉-n 4-[N(CH₃)₂]—Ph CH₂CH₂ 206 CH₃ 4-[N(CH₃)₂]—Ph CH(CH₃)CH₂ 207 C₂H₅ 4-[N(CH₃)₂]—Ph CH(CH₃)CH₂ 208 C₃H₇-n 4-[N(CH₃)₂]—Ph CH(CH₃)CH₂ 209 C₃H₇-i 4-[N(CH₃)₂]—Ph CH(CH₃)CH₂ 210 C₄H₉-n 4-[N(CH₃)₂]—Ph CH(CH₃)CH₂ 211 CH₃ 4-CN—Ph CH₂CH₂ 212 C₂H₅ 4-CN—Ph CH₂CH₂ 213 C₃H₇-n 4-CN—Ph CH₂CH₂ 214 C₃H₇-i 4-CN—Ph CH₂CH₂ 215 C₄H₉-n 4-CN—Ph CH₂CH₂ 216 CH₃ 4-CN—Ph CH(CH₃)CH₂ 217 C₂H₅ 4-CN—Ph CH(CH₃)CH₂ 218 C₃H₇-n 4-CN—Ph CH(CH₃)CH₂ 219 C₃H₇-i 4-CN—Ph CH(CH₃)CH₂ 220 C₄H₉-n 4-CN—Ph CH(CH₃)CH₂ 221 CH₃

CH₂CH₂ 222 C₂H₅

CH₂CH₂ 223 C₃H₇-n

CH₂CH₂ 224 C₃H₇-i

CH₂CH₂ 225 C₄H₉-n

CH₂CH₂ 226 CH₃

CH(CH₃)CH₂ 227 C₂H₅

CH(CH₃)CH₂ 228 C₃H₇-n

CH(CH₃)CH₂ 229 C₃H₇-i

CH(CH₃)CH₂ 230 C₄H₉-n

CH(CH₃)CH₂ 231 CH₃

CH₂CH₂ 232 C₂H₅

CH₂CH₂ 233 C₃H₇-n

CH₂CH₂ 234 C₃H₇-i

CH₂CH₂ 235 C₄H₉-n

CH₂CH₂ 236 CH₃

CH(CH₃)CH₂ 237 C₂H₅

CH(CH₃)CH₂ 238 C₃H₇-n

CH(CH₃)CH₂ 239 C₃H₇-i

CH(CH₃)CH₂ 240 C₄H₉-n

CH(CH₃)CH₂ 241 CH₃

CH₂CH₂ 242 C₂H₅

CH₂CH₂ 243 C₃H₇-n

CH₂CH₂ 244 C₃H₇-i

CH₂CH₂ 245 C₄H₉-n

CH₂CH₂ 246 CH₃

CH(CH₃)CH₂ 247 C₂H₅

CH(CH₃)CH₂ 248 C₃H₇-n

CH(CH₃)CH₂ 249 C₃H₇-i

CH(CH₃)CH₂ 250 C₄H₉-n

CH(CH₃)CH₂ 251 CH₃ 4-C₃H₇-i-Ph CH₂CH₂ 252 C₂H₅ 4-C₃H₇-i-Ph CH₂CH₂ 253 C₃H₇-n 4-C₃H₇-i-Ph CH₂CH₂ 254 C₃H₇-i 4-C₃H₇-i-Ph CH₂CH₂ 255 C₄H₉-n 4-C₃H₇-i-Ph CH₂CH₂ 256 CH₃ 4-C₃H₇-i-Ph CH(CH₃)CH₂ 257 C₂H₅ 4-C₃H₇-i-Ph CH(CH₃)CH₂ 258 C₃H₇-n 4-C₃H₇-i-Ph CH(CH₃)CH₂ 259 C₃H₇-i 4-C₃H₇-i-Ph CH(CH₃)CH₂ 260 C₄H₉-n 4-C₃H₇-i-Ph CH(CH₃)CH₂ 261 CH₃ 4-C₄H₉-t-Ph CH₂CH₂ 262 C₂H₅ 4-C₄H₉-t-Ph CH₂CH₂ 263 C₃H₇-n 4-C₄H₉-t-Ph CH₂CH₂ 264 C₃H₇-i 4-C₄H₉-t-Ph CH₂CH₂ 265 C₄H₉-n 4-C₄H₉-t-Ph CH₂CH₂ 266 CH₃ 4-C₄H₉-t-Ph CH(CH₃)CH₂ 267 C₂H₅ 4-C₄H₉-t-Ph CH(CH₃)CH₂ 268 C₃H₇-n 4-C₄H₉-t-Ph CH(CH₃)CH₂ 269 C₃H₇-i 4-C₄H₉-t-Ph CH(CH₃)CH₂ 270 C₄H₉-n 4-C₄H₉-t-Ph CH(CH₃)CH₂ 271 CH₃

CH₂CH₂ 272 C₂H₅

CH₂CH₂ 273 C₃H₇-n

CH₂CH₂ 274 C₃H₇-i

CH₂CH₂ 275 C₄H₉-n

CH₂CH₂ 276 CH₃

CH(CH₃)CH₂ 277 C₂H₅

CH(CH₃)CH₂ 278 C₃H₇-n

CH(CH₃)CH₂ 279 C₃H₇-i

CH(CH₃)CH₂ 280 C₄H₉-n

CH(CH₃)CH₂ 281 CH₃

CH₂CH₂ 282 C₂H₅

CH₂CH₂ 283 C₃H₇-n

CH₂CH₂ 284 C₃H₇-i

CH₂CH₂ 285 C₄H₉-n

CH₂CH₂ 286 CH₃

CH(CH₃)CH₂ 287 C₂H₅

CH(CH₃)CH₂ 288 C₃H₇-n

CH(CH₃)CH₂ 289 C₃H₇-i

CH(CH₃)CH₂ 290 C₄H₉-n

CH(CH₃)CH₂ 291 CH₃

CH₂CH₂ 292 C₂H₅

CH₂CH₂ 293 C₃H₇-n

CH₂CH₂ 294 C₃H₇-i

CH₂CH₂ 295 C₄H₉-n

CH₂CH₂ 296 CH₃

CH(CH₃)CH₂ 297 C₂H₅

CH(CH₃)CH₂ 298 C₃H₇-n

CH(CH₃)CH₂ 299 C₃H₇-i

CH(CH₃)CH₂ 300 C₄H₉-n

CH(CH₃)CH₂ 301 CH₃

CH₂CH₂ 302 C₂H₅

CH₂CH₂ 303 C₃H₇-n

CH₂CH₂ 304 C₃H₇-i

CH₂CH₂ 305 C₄H₉-n

CH₂CH₂ 306 CH₃

CH(CH₃)CH₂ 307 C₂H₅

CH(CH₃)CH₂ 308 C₃H₇-n

CH(CH₃)CH₂ 309 C₃H₇-i

CH(CH₃)CH₂ 310 C₄H₉-n

CH(CH₃)CH₂ 311 CH₃

CH₂CH₂ 312 C₂H₅

CH₂CH₂ 313 C₃H₇-n

CH₂CH₂ 314 C₃H₇-i

CH₂CH₂ 315 C₄H₉-n

CH₂CH₂ 316 CH₃

CH(CH₃)CH₂ 317 C₂H₅

CH(CH₃)CH₂ 318 C₃H₇-n

CH(CH₃)CH₂ 319 C₃H₇-i

CH(CH₃)CH₂ 320 C₄H₉-n

CH(CH₃)CH₂ 321 CH₃ 3′,4′-Cl₂—Ph-4-Ph CH₂CH₂ 322 C₂H₅ 3′,4′-Cl₂—Ph-4-Ph CH₂CH₂ 323 C₃H₇-n 3′,4′-Cl₂—Ph-4-Ph CH₂CH₂ 324 C₃H₇-i 3′,4′-Cl₂—Ph-4-Ph CH₂CH₂ 325 C₄H₉-n 3′,4′-Cl₂—Ph-4-Ph CH₂CH₂ 326 CH₃ 3′,4′-Cl₂—Ph-4-Ph CH(CH₃)CH₂ 327 C₂H₅ 3′,4′-Cl₂—Ph-4-Ph CH(CH₃)CH₂ 328 C₃H₇-n 3′,4′-Cl₂—Ph-4-Ph CH(CH₃)CH₂ 329 C₃H₇-i 3′,4′-Cl₂—Ph-4-Ph CH(CH₃)CH₂ 330 C₄H₉-n 3′,4′-Cl₂—Ph-4-Ph CH(CH₃)CH₂ 331 CH₃ 4′-CF₃—Ph-4-Ph CH₂CH₂ 332 C₂H₅ 4′-CF₃—Ph-4-Ph CH₂CH₂ 333 C₃H₇-n 4′-CF₃—Ph-4-Ph CH₂CH₂ 334 C₃H₇-i 4′-CF₃—Ph-4-Ph CH₂CH₂ 335 C₄H₉-n 4′-CF₃—Ph-4-Ph CH₂CH₂ 336 CH₃ 4′-CF₃—Ph-4-Ph CH(CH₃)CH₂ 337 C₂H₅ 4′-CF₃—Ph-4-Ph CH(CH₃)CH₂ 338 C₃H₇-n 4′-CF₃—Ph-4-Ph CH(CH₃)CH₂ 339 C₃H₇-i 4′-CF₃—Ph-4-Ph CH(CH₃)CH₂ 340 C₄H₉-n 4′-CF₃—Ph-4-Ph CH(CH₃)CH₂ 341 CH₃ 4′-CF₃—O—Ph-4-Ph CH₂CH₂ 342 C₂H₅ 4′-CF₃—O—Ph-4-Ph CH₂CH₂ 343 C₃H₇-n 4′-CF₃—O—Ph-4-Ph CH₂CH₂ 344 C₃H₇-i 4′-CF₃—O—Ph-4-Ph CH₂CH₂ 345 C₄H₉-n 4′-CF₃—O—Ph-4-Ph CH₂CH₂ 346 CH₃ 4′-CF₃—O—Ph-4-Ph CH(CH₃)CH₂ 347 C₂H₅ 4′-CF₃—O—Ph-4-Ph CH(CH₃)CH₂ 348 C₃H₇-n 4′-CF₃—O—Ph-4-Ph CH(CH₃)CH₂ 349 C₃H₇-i 4′-CF₃—O—Ph-4-Ph CH(CH₃)CH₂ 350 C₄H₉-n 4′-CF₃—O—Ph-4-Ph CH(CH₃)CH₂ 351 CH₃ 4′-C₄H₉-t-Ph-4-Ph CH₂CH₂ 352 C₂H₅ 4′-C₄H₉-t-Ph-4-Ph CH₂CH₂ 353 C₃H₇-n 4′-C₄H₉-t-Ph-4-Ph CH₂CH₂ 354 C₃H₇-i 4′-C₄H₉-t-Ph-4-Ph CH₂CH₂ 355 C₄H₉-n 4′-C₄H₉-t-Ph-4-Ph CH₂CH₂ 356 CH₃ 4′-C₄H₉-t-Ph-4-Ph CH(CH₃)CH₂ 357 C₂H₅ 4′-C₄H₉-t-Ph-4-Ph CH(CH₃)CH₂ 358 C₃H₇-n 4′-C₄H₉-t-Ph-4-Ph CH(CH₃)CH₂ 359 C₃H₇-i 4′-C₄H₉-t-Ph-4-Ph CH(CH₃)CH₂ 360 C₄H₉-n 4′-C₄H₉-t-Ph-4-Ph CH(CH₃)CH₂ 361 CH₃ 4′-F—Ph-4-Ph CH₂CH₂ 362 C₂H₅ 4′-F—Ph-4-Ph CH₂CH₂ 363 C₃H₇-n 4′-F—Ph-4-Ph CH₂CH₂ 364 C₃H₇-i 4′-F—Ph-4-Ph CH₂CH₂ 365 C₄H₉-n 4′-F—Ph-4-Ph CH₂CH₂ 366 CH₃ 4′-F—Ph-4-Ph CH(CH₃)CH₂ 367 C₂H₅ 4′-F—Ph-4-Ph CH(CH₃)CH₂ 368 C₃H₇-n 4′-F—Ph-4-Ph CH(CH₃)CH₂ 369 C₃H₇-i 4′-F—Ph-4-Ph CH(CH₃)CH₂ 370 C₄H₉-n 4′-F—Ph-4-Ph CH(CH₃)CH₂ 371 CH₃ 3′-CH₃—O—Ph-4-Ph CH₂CH₂ 372 C₂H₅ 3′-CH₃—O—Ph-4-Ph CH₂CH₂ 373 C₃H₇-n 3′-CH₃—O—Ph-4-Ph CH₂CH₂ 374 C₃H₇-i 3′-CH₃—O—Ph-4-Ph CH₂CH₂ 375 C₄H₉-n 3′-CH₃—O—Ph-4-Ph CH₂CH₂ 376 CH₃ 3′-CH₃—O—Ph-4-Ph CH(CH₃)CH₂ 377 C₂H₅ 3′-CH₃—O—Ph-4-Ph CH(CH₃)CH₂ 378 C₃H₇-n 3′-CH₃—O—Ph-4-Ph CH(CH₃)CH₂ 379 C₃H₇-i 3′-CH₃—O—Ph-4-Ph CH(CH₃)CH₂ 380 C₄H₉-n 3′-CH₃—O—Ph-4-Ph CH(CH₃)CH₂

TABLE C W Z 001 O Ph 002 O

003 CH₂O 2-CH₃—Ph 004 CH₂O 2,5-di-CH₃—Ph 005 CH₂O

006 CH₂O

007 CH₂ON═C(CH₃) Ph 008 CH₂ON═C(CH₃) 4-Cl—Ph 009 CH₂ON═C(CH₃) 4-CF₃—Ph 010 CH₂ON═C(CH₃) 3-CF₃—Ph 011 CH₂ON═C(CH₃) 3-CF₃O—Ph 012 CH₂ON═C-cycl-C₃H₇ 4-Cl—Ph 013 CH₂ON═C-cycl-C₃H₇ 4-F—Ph 014 CH₂ON═C-cycl-C₃H₇ 3-CH₃-4-Cl—Ph 015 CH₂ON═C(CH₃)C═NOCH₃ CH₃ 016 CH₂ON═C(CH₃)C═NOCH₃ OCH(CH₃)₂ 017 CH₂ON═C(CH₃)C═NOCH₃ Ph 018 CH₂ON═C(CH₃)C═NOCH₃ 4-F—Ph 019 CH₂ON═C(CH₃)C═NOCH₃ 4-Cl—Ph 020 CH₂ON═C(CH₃)C═NOCH₃ 4-Br—Ph 021 CH₂ON═C(CH₃)C═NOCH₃ 4-CH₃—Ph 022 CH₂ON═C(CH₃)C═NOCH₃ 4-CH₃O—Ph 023 CH₂ON═C(CH₃)C═NOCH₃ 4-CN—Ph 024 CH₂ON═C(CH₃)C═NOCH₃ 3-CF₃—Ph 025 CH₂ON═C(CH₃)C═NOCH₃

026 CH₂ON═C(CH₃)C═NOCH₃

027 CH₂ON═C(CH₃)C═NOCH₃ 2,4-di-F—Ph 028 CH═NOCH(CN) 3-CF₃—Ph 029 CH═NOCH(CH₃) Ph 030 CH═NOCH(CH₃) 2-Cl—Ph 031 CH═NOCH(CH₃) 3-Cl—Ph 032 CH═NOCH(CH₃) 4-Cl—Ph 033 CH═NOCH(CH₃) 2-CN—Ph 034 CH═NOCH(CH₃) 3-CF₃—Ph 035 CH═NOCH(CH₃) 4-CF₃—Ph 036 CH═NOCH(CH₃) Ph 037 CH═NOCH(CH₃) 4-Cl—Ph 038 CH═N—N═C(CH₃)C═NOCH₃ CH₃ 039 CH═N—N═C(CH₃)C═NOCH₃ OCH(CH₃)₂ 040 CH═N—N═C(CH₃)C═NOCH₃ Ph 041 CH═N—N═C(CH₃)C═NOCH₃ 4-F—Ph 042 CH═N—N═C(CH₃)C═NOCH₃ 4-Cl—Ph 043 CH═N—N═C(CH₃)C═NOCH₃ 4-Br—Ph 044 CH═N—N═C(CH₃)C═NOCH₃ 4-CH₃—Ph 045 CH═N—N═C(CH₃)C═NOCH₃ 4-OCH₃—Ph 046 CH═N—N═C(CH₃)C═NOCH₃ 4-CN—Ph 047 CH═N—N═C(CH₃)C═NOCH₃ 3-CF3—Ph 048 CH═N—N═C(CH₃)C═NOCH₃ 2-Pyridyl 050 CH═N—N═C(CH₃)C═NOCH₃ 4-Pyridyl 051 O

052 CH₂O

053 CH₂ON═C(CH₃) 3-CF₃—Ph

TABLE D R A 001 CH₃ 4-Cl—Ph 002 C₂H₅ 4-Cl—Ph 003 C₃H₇-n 4-Cl—Ph 004 C₃H₇-i 4-Cl—Ph 005 C₄H₉-n 4-Cl—Ph 006 CH₃ 4-Cl—Ph 007 C₂H₅ 4-Cl—Ph 008 C₃H₇-n 4-Cl—Ph 009 C₃H₇-i 4-Cl—Ph 010 C₄H₉-n 4-Cl—Ph 011 CH₃ 3,4-di-Cl—Ph 012 C₂H₅ 3,4-di-Cl—Ph 013 C₃H₇-n 3,4-di-Cl—Ph 014 C₃H₇-i 3,4-di-Cl—Ph 015 C₄H₉-n 3,4-di-Cl—Ph 016 CH₃ 3,4-di-Cl—Ph 017 C₂H₅ 3,4-di-Cl—Ph 018 C₃H₇-n 3,4-di-Cl—Ph 019 C₃H₇-i 3,4-di-Cl—Ph 020 C₄H₉-n 3,4-di-Cl—Ph 021 CH₃ Ph 022 C₂H₅ Ph 023 C₃H₇-n Ph 024 C₃H₇-i Ph 025 C₄H₉-n Ph 026 CH₃ Ph 027 C₂H₅ Ph 028 C₃H₇-n Ph 029 C₃H₇-i Ph 030 C₄H₉-n Ph 031 CH₃ 4-Br—Ph 032 C₂H₅ 4-Br—Ph 033 C₃H₇-n 4-Br—Ph 034 C₃H₇-i 4-Br—Ph 035 C₄H₉-n 4-Br—Ph 036 CH₃ 4-Br—Ph 037 C₂H₅ 4-Br—Ph 038 C₃H₇-n 4-Br—Ph 039 C₃H₇-i 4-Br—Ph 040 C₄H₉-n 4-Br—Ph 041 CH₃ 4-CH₃—Ph 042 C₂H₅ 4-CH₃—Ph 043 C₃H₇-n 4-CH₃—Ph 044 C₃H₇-i 4-CH₃—Ph 045 C₄H₉-n 4-CH₃—Ph 046 CH₃ 4-CH₃—Ph 047 C₂H₅ 4-CH₃—Ph 048 C₃H₇-n 4-CH₃—Ph 049 C₃H₇-i 4-CH₃—Ph 050 C₄H₉-n 4-CH₃—Ph 051 CH₃ 4-CH₃O—Ph 052 C₂H₅ 4-CH₃O—Ph 053 C₃H₇-n 4-CH₃O—Ph 054 C₃H₇-i 4-CH₃O—Ph 055 C₄H₉-n 4-CH₃O—Ph 056 CH₃ 4-CH₃O—Ph 057 C₂H₅ 4-CH₃O—Ph 058 C₃H₇-n 4-CH₃O—Ph 059 C₃H₇-i 4-CH₃O—Ph 060 C₄H₉-n 4-CH₃O—Ph 061 CH₃ 4-CF₃—Ph 062 C₂H₅ 4-CF₃—Ph 063 C₃H₇-n 4-CF₃—Ph 064 C₃H₇-i 4-CF₃—Ph 065 C₄H₉-n 4-CF₃—Ph 066 CH₃ 4-CF₃—Ph 067 C₂H₅ 4-CF₃—Ph 068 C₃H₇-n 4-CF₃—Ph 069 C₃H₇-i 4-CF₃—Ph 070 C₄H₉-n 4-CF₃—Ph 071 CH₃ 4-F—Ph 072 C₂H₅ 4-F—Ph 073 C₃H₇-n 4-F—Ph 074 C₃H₇-i 4-F—Ph 075 C₄H₉-n 4-F—Ph 076 CH₃ 4-F—Ph 077 C₂H₅ 4-F—Ph 078 C₃H₇-n 4-F—Ph 079 C₃H₇-i 4-F—Ph 080 C₄H₉-n 4-F—Ph 081 CH₃ 4-CF₃O—Ph 082 C₂H₅ 4-CF₃O—Ph 083 C₃H₇-n 4-CF₃O—Ph 084 C₃H₇-i 4-CF₃O—Ph 085 C₄H₉-n 4-CF₃O—Ph 086 CH₃ 4-CF₃O—Ph 087 C₂H₅ 4-CF₃O—Ph 088 C₃H₇-n 4-CF₃O—Ph 089 C₃H₇-i 4-CF₃O—Ph 090 C₄H₉-n 4-CF₃O—Ph 091 CH₃ 3,4-di-OCH₃—Ph 092 C₂H₅ 3,4-di-OCH₃—Ph 093 C₃H₇-n 3,4-di-OCH₃—Ph 094 C₃H₇-i 3,4-di-OCH₃—Ph 095 C₄H₉-n 3,4-di-OCH₃—Ph 096 CH₃ 3,4-di-OCH₃—Ph 097 C₂H₅ 3,4-di-OCH₃—Ph 098 C₃H₇-n 3,4-di-OCH₃—Ph 099 C₃H₇-i 3,4-di-OCH₃—Ph 100 C₄H₉-n 3,4-di-OCH₃—Ph 101 CH₃ 3,4-OCH₂—O—Ph 102 C₂H₅ 3,4-OCH₂—O—Ph 103 C₃H₇-n 3,4-OCH₂—O—Ph 104 C₃H₇-i 3,4-OCH₂—O—Ph 105 C₄H₉-n 3,4-OCH₂—O—Ph 106 CH₃ 3,4-OCH₂—O—Ph 107 C₂H₅ 3,4-OCH₂—O—Ph 108 C₃H₇-n 3,4-OCH₂—O—Ph 109 C₃H₇-i 3,4-OCH₂—O—Ph 110 C₄H₉-n 3,4-OCH₂—O—Ph 111 CH₃ 3,4-di-F—Ph 112 C₂H₅ 3,4-di-F—Ph 113 C₃H₇-n 3,4-di-F—Ph 114 C₃H₇-i 3,4-di-F—Ph 115 C₄H₉-n 3,4-di-F—Ph 116 CH₃ 3,4-di-F—Ph 117 C₂H₅ 3,4-di-F—Ph 118 C₃H₇-n 3,4-di-F—Ph 119 C₃H₇-i 3,4-di-F—Ph 120 C₄H₉-n 3,4-di-F—Ph 121 CH₃

122 C₂H₅

123 C₃H₇-n

124 C₃H₇-i

125 C₄H₉-n

126 CH₃

127 C₂H₅

128 C₃H₇-n

129 C₃H₇-i

130 C₄H₉-n

131 CH₃

132 C₂H₅

133 C₃H₇-n

134 C₃H₇-i

135 C₄H₉-n

136 CH₃

137 C₂H₅

138 C₃H₇-n

139 C₃H₇-i

140 C₄H₉-n

141 CH₃

142 C₂H₅

143 C₃H₇-n

144 C₃H₇-i

145 C₄H₉-n

146 CH₃

147 C₂H₅

148 C₃H₇-n

149 C₃H₇-i

150 C₄H₉-n

151 CH₃ 4-Ph—Ph 152 C₂H₅ 4-Ph—Ph 153 C₃H₇-n 4-Ph—Ph 154 C₃H₇-i 4-Ph—Ph 155 C₄H₉-n 4-Ph—Ph 156 CH₃ 4-Ph—Ph 157 C₂H₅ 4-Ph—Ph 158 C₃H₇-n 4-Ph—Ph 159 C₃H₇-i 4-Ph—Ph 160 C₄H₉-n 4-Ph—Ph 161 CH₃ 4′-Cl—Ph-4-Ph 162 C₂H₅ 4′-Cl—Ph-4-Ph 163 C₃H₇-n 4′-Cl—Ph-4-Ph 164 C₃H₇-i 4′-Cl—Ph-4-Ph 165 C₄H₉-n 4′-Cl—Ph-4-Ph 166 CH₃ 4′-Cl—Ph-4-Ph 167 C₂H₅ 4′-Cl—Ph-4-Ph 168 C₃H₇-n 4′-Cl—Ph-4-Ph 169 C₃H₇-i 4′-Cl—Ph-4-Ph 170 C₄H₉-n 4′-Cl—Ph-4-Ph 171 CH₃ 4′-CH₃—Ph-4-Ph 172 C₂H₅ 4′-CH₃—Ph-4-Ph 173 C₃H₇-n 4′-CH₃—Ph-4-Ph 174 C₃H₇-i 4′-CH₃—Ph-4-Ph 175 C₄H₉-n 4′-CH₃—Ph-4-Ph 176 CH₃ 4′-CH₃—Ph-4-Ph 177 C₂H₅ 4′-CH₃—Ph-4-Ph 178 C₃H₇-n 4′-CH₃—Ph-4-Ph 179 C₃H₇-i 4′-CH₃—Ph-4-Ph 180 C₄H₉-n 4′-CH₃—Ph-4-Ph 181 CH₃ 3,4-di-CH₃—Ph 182 C₂H₅ 3,4-di-CH₃—Ph 183 C₃H₇-n 3,4-di-CH₃—Ph 184 C₃H₇-i 3,4-di-CH₃—Ph 185 C₄H₉-n 3,4-di-CH₃—Ph 186 CH₃ 3,4-di-CH₃—Ph 187 C₂H₅ 3,4-di-CH₃—Ph 188 C₃H₇-n 3,4-di-CH₃—Ph 189 C₃H₇-i 3,4-di-CH₃—Ph 190 C₄H₉-n 3,4-di-CH₃—Ph 191 CH₃ 4-cycl-C₆H₁₁—Ph 192 C₂H₅ 4-cycl-C₆H₁₁—Ph 193 C₃H₇-n 4-cycl-C₆H₁₁—Ph 194 C₃H₇-i 4-cycl-C₆H₁₁—Ph 195 C₄H₉-n 4-cycl-C₆H₁₁—Ph 196 CH₃ 4-cycl-C₆H₁₁—Ph 197 C₂H₅ 4-cycl-C₆H₁₁—Ph 198 C₃H₇-n 4-cycl-C₆H₁₁—Ph 199 C₃H₇-i 4-cycl-C₆H₁₁—Ph 200 C₄H₉-n 4-cycl-C₆H₁₁—Ph 201 CH₃ 4-[N(CH₃)₂]—Ph 202 C₂H₅ 4-[N(CH₃)₂]—Ph 203 C₃H₇-n 4-[N(CH₃)₂]—Ph 204 C₃H₇-i 4-[N(CH₃)₂]—Ph 205 C₄H₉-n 4-[N(CH₃)₂]—Ph 206 CH₃ 4-[N(CH₃)₂]—Ph 207 C₂H₅ 4-[N(CH₃)₂]—Ph 208 C₃H₇-n 4-[N(CH₃)₂]—Ph 209 C₃H₇-i 4-[N(CH₃)₂]—Ph 210 C₄H₉-n 4-[N(CH₃)₂]—Ph 211 CH₃ 4-CN—Ph 212 C₂H₅ 4-CN—Ph 213 C₃H₇-n 4-CN—Ph 214 C₃H₇-i 4-CN—Ph 215 C₄H₉-n 4-CN—Ph 216 CH₃ 4-CN—Ph 217 C₂H₅ 4-CN—Ph 218 C₃H₇-n 4-CN—Ph 219 C₃H₇-i 4-CN—Ph 220 C₄H₉-n 4-CN—Ph 221 CH₃

222 C₂H₅

223 C₃H₇-n

224 C₃H₇-i

225 C₄H₉-n

226 CH₃

227 C₂H₅

228 C₃H₇-n

229 C₃H₇-i

230 C₄H₉-n

231 CH₃

232 C₂H₅

233 C₃H₇-n

234 C₃H₇-i

235 C₄H₉-n

236 CH₃

237 C₂H₅

238 C₃H₇-n

239 C₃H₇-i

240 C₄H₉-n

241 CH₃

242 C₂H₅

243 C₃H₇-n

244 C₃H₇-i

245 C₄H₉-n

246 CH₃

247 C₂H₅

248 C₃H₇-n

249 C₃H₇-i

250 C₄H₉-n

251 CH₃ 4-C₃H₇-i-Ph 252 C₂H₅ 4-C₃H₇-i-Ph 253 C₃H₇-n 4-C₃H₇-i-Ph 254 C₃H₇-i 4-C₃H₇-i-Ph 255 C₄H₉-n 4-C₃H₇-i-Ph 256 CH₃ 4-C₃H₇-i-Ph 257 C₂H₅ 4-C₃H₇-i-Ph 258 C₃H₇-n 4-C₃H₇-i-Ph 259 C₃H₇-i 4-C₃H₇-i-Ph 260 C₄H₉-n 4-C₃H₇-i-Ph 261 CH₃ 4-C₄H₉-t-Ph 262 C₂H₅ 4-C₄H₉-t-Ph 263 C₃H₇-n 4-C₄H₉-t-Ph 264 C₃H₇-i 4-C₄H₉-t-Ph 265 C₄H₉-n 4-C₄H₉-t-Ph 266 CH₃ 4-C₄H₉-t-Ph 267 C₂H₅ 4-C₄H₉-t-Ph 268 C₃H₇-n 4-C₄H₉-t-Ph 269 C₃H₇-i 4-C₄H₉-t-Ph 270 C₄H₉-n 4-C₄H₉-t-Ph 271 CH₃

272 C₂H₅

273 C₃H₇-n

274 C₃H₇-i

275 C₄H₉-n

276 CH₃

277 C₂H₅

278 C₃H₇-n

279 C₃H₇-i

280 C₄H₉-n

281 CH₃

282 C₂H₅

283 C₃H₇-n

284 C₃H₇-i

285 C₄H₉-n

286 CH₃

287 C₂H₅

288 C₃H₇-n

289 C₃H₇-i

290 C₄H₉-n

291 CH₃

292 C₂H₅

293 C₃H₇-n

294 C₃H₇-i

295 C₄H₉-n

296 CH₃

297 C₂H₅

298 C₃H₇-n

299 C₃H₇-i

300 C₄H₉-n

301 CH₃

302 C₂H₅

303 C₃H₇-n

304 C₃H₇-i

305 C₄H₉-n

306 CH₃

307 C₂H₅

308 C₃H₇-n

309 C₃H₇-i

310 C₄H₉-n

311 CH₃

312 C₂H₅

313 C₃H₇-n

314 C₃H₇-i

315 C₄H₉-n

316 CH₃

317 C₂H₅

318 C₃H₇-n

319 C₃H₇-i

320 C₄H₉-n

Selected Physico-chemical Data

Compound No. Melting Point, ¹H-NMR, or Molpeak (ESMS) 01.259 485 (M + HCOO)⁻ 01.260 625 (M + HCOO)⁻ 11.151 oil 11.161 oil 11.171 mp: 40-47° C. 11.321 oil 11.331 oil 11.341 oil 11.351 mp: 45-52° C. 11.361 oil 11.371 oil 12.131 457/459 (M+ 1)⁺ 12.141 379 (M + 1)⁺ 13.011 451 (M − 1)⁻ 14.001 415 (M − 1)⁻ 14.002 431 (M + 1)⁺ 14.011 449 (M − 1)⁻ 14.012 509 (M + HCOO)⁻ 14.031 459/461 (M − 1)⁻ 14.041 397 (M + 1)⁺ 14.042 411 (M + 1)⁺ 14.051 413 (M + 1)⁺ 14.071 401 (M + 1)⁺ 14.091 443 (M + 1)⁺ 14.101 427 (M + 1)⁺ 14.111 417 (M − 1)⁻ 14.121 433 (M + 1)⁺ 14.131 465 (M − 1)⁻ 14.311 467 (M + 1)⁺ 17.011 477 (M − 1)⁻ 22.011 561 (M + 1)⁺ 22.041 507 (M + 1)⁺ 26.011 615 (M + HCOO)⁻ 30.008 d (¹H-NMR,CDCl₃): 2.7 ppm (SMe) 30.010 mp:118-119° C.

Formulations may be prepared analogously to those described in, for example, WO 95/30651.

Biological Examples D-1: Action against Plasmopara viticola on Vines

a) Residual-protective Action

Vine seedlings are sprayed at the 4- to 5-leaf stage with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After 24 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation for 6 days at 95-100% relative humidity and 20° C.

b) Residual-curative Action

Vine seedlings are infected at the 4- to 5-leaf stage with a sporangia suspension of the fungus. After incubation for 24 hours in a humidity chamber at 95-100% relative humidity and 20° C., the infected plants are dried and sprayed with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After the spray coating has dried, the treated plants are placed in the humidity chamber again. Fungus infestation is evaluated 6 days after infection.

Compounds of Tables 1 to 40 exhibit a good fungicidal action against Plasmopara viticola on vines. Compounds 11.171, 11.351, 12.001, 13.011, 14.001, 14.011, 14.031, 14.041, 14.042, 14.051, 14.071, 14.121, 17.011, 30.008 and 30.010 completely inhibit fungal infestation in this test.

D-2: Action Against Phytophthora on Tomato Plants

a) Residual-protective Action

After a cultivation period of 3 weeks, tomato plants are sprayed with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 5 days at 90-100% relative humidity and 20° C.

b) Systemic Action

After a cultivation period of 3 weeks, tomato plants are watered with a spray mixture (0.02% active ingredient based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above the ground. After 96 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100% relative humidity and 20° C. Compounds of Tables 1 to 40 exhibit a long-lasting effect against fungus infestation. Compounds 13.011, 14.001, 14.011, 14.031, 14.041, 14.042, 17.011 and 30.008 completely inhibit fungal infestation in this test.

D-3: Action Against Phytophthora on Potato Plants

a) Residual-protective Action

2-3 week old potato plants (Bintje variety) are sprayed with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100% relative humidity and 20° C.

b) Systemic Action

2-3 week old potato plants (Bintje variety) are watered with a spray mixture (0.02% active ingredient based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above the ground. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100% relative humidity and 20° C.

Compounds of Tables 1 to 40 exhibit a good fungicidal action against Phytophthora on potatoes. Compounds 14.001, 14.011, 14.041 and 30.008 completely inhibit fungal infestation in this test. 

What is claimed is:
 1. A α-sulfenimino acid derivative of formula I

Including the optical isomers thereof and mixtures of such isomers, wherein A is cycloalkyl, cycloalkenyl or aryl, each optionally substituted, B is a direct bond or optionally substituted alkylene, E is optionally substituted aryl, R is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each optionally substituted, and T is NH.
 2. A compound according to claim 1 wherein A is phenyl, naphthyl, cycloalkyl or cycloalkenyl, wherein each of the cycles is optionally mono- or poly-substituted by substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈cycloalkyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkanoyloxy, C_(l-8)-alkoxycarbonyl, C₃₋₈-alkenyloxycarbonyl, C₃₋₈-alkynyloxycarbonyl, C₁₋₈-dialkylamino, C₁₋₈-alkylamino, C₁₋₈-hydroximinoalkyl and C₁₋₈-alkoximinoalkyl wherein each of the alkyl, alkenyl, alkynyl moieties are straight-chain or branched and may in turn be optionally halogenated; halogen; nitro; cyano; hydroxy; amino; formyl; carboxyl; carbamoyl and thiocarbamoyl; or from the group comprising aryl, aryloxy, arylthio, aryl-C₁₋₄-alkyl, aryl-C₁₋₄-alkyloxy or aryl-C₁₋₄-alkylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; or from the group comprising aryloxyalkyl, arylalkyliminoxyalkyl, aryloxyiminoalkyl, arylalkyloxylminoalkyl, aryloxyiminoalkyleniminoxyalkyl and aryl-alkyloxyiminoalkyleniminoxyalkyl wherein each alkyl or alkylene may be straight-chain or branched and each aryl may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-calkylthio; and B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising halogen, linear or branched C₁₋₆-alkyl, C₂₋₈-alkenyl or C₂₋₈-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; and E is phenyl optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-cycloalkyloxy, C₈₋₁₀-aryloxy, C₈₋₁₀-aryl-C₁₋₈-alkyloxy, C₆₋₁₀-aryl-C₃₋₈-alkenyloxy, C₈₋₁₀-aryl-C₃₋₆-alkynyloxy, C₁₋₈-alkanoyloxy, C₃₋₈-cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₃₋₈-alklyloxycarbonyl and C₃₋₈-alkinyloxycarbonyl wherein in each of the preceding groups the alkyl, alkenyl, alkynyl or cycloalkyl part may be partially or fully halogenated and wherein the aryl groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; halogen, nitro, cyano, hydroxy, amino, di C₁₋₈-alkylamino and C₁₋₈-alkylamino; and R is hydrogen or C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₈-alkyl, C₆₋₁₀-aryl or C₆₋₁₀-aryl-C₁₋₈-alkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₆-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkylsulfonyl, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₃₋₈-alkenyloxycarbonyl and C₃₋₈-alkyl-nyloxycarbonyl wherein each of the alkyl, alkenyl, alkynyl or cycloalkyl parts of the preceding substituents may be partially or fully halogenated; halogen, nitro and cyano.
 3. A compound of formula I according to claim 1 wherein A is phenyl or naphthyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy, arylthio, aryl-C₁₋₄-alkyl, aryl-C₁₋₄-alkyloxy or aryl-C₁₋₄-alkylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; or from the group comprising phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxyimino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising F, Cl, Br, linear or branched C₁₋₄-alkyl, C₁₋₄-alkenyl or, C₂₋₄-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; and E is phenyl optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, phenyl-C₁₋₈-alkyloxy, phenyl-C₃₋₈-alkenyloxy, phenyl-C₃₋₈-alkynyloxy, C₃₋₈-cycloalkyl-C₃₋₆alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxy, C₃₋₈-haloalkenyloxy, halogen and cyano, wherein the phenyl groups may be optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; and R is C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl or C₁₋₄-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkanoyl, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano.
 4. A compound of formula I according to claim 1 wherein A is phenyl or naphthyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₈-alkyl, C₂₋₈-alkenyl, C₃₋₈-cycloalkyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-haloalkoxy, C₁₋₈-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy or arylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; or from a group comprising phenoxy-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyliminoxy-C₁₋₄-alkyl and phenyl-alkoxylmino-C₂₋₄-alkyleniminoxy-C₁₋₄-alkyl wherein each alkyl or alkylene may be straight-chain or branched and each phenyl or phenoxy may in turn be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is a direct bond or C₁₋₄-alkylene which is optionally substituted with substituents selected from the group comprising F, Cl, Br, linear or branched C₁₋₂-alkyl, C₂₋₃-alkenyl or, C₂₋₃-alkynyl and C₅₋₇-cycloalkyl, each in turn optionally substituted with 1-4 halogen atoms; and E is phenyl optionally di- to tri-substituted with substituents selected from the group comprising C₁₋₈-alkyl, C₁₋₈-alkoxy, C₃₋₈-alkenyloxy, C₃₋₈-alkynyloxy, phenyl-C₁₋₆-alkyloxy, phenyl-C₃₋₆-alkenyloxy, phenyl-C₃₋₈-alkynyloxy, C₃₋₈-cycloalkyl-C₃₋₆-alkynyloxy, C₁₋₈-alkylthio, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxy, C₃₋₈-haloalkenyloxy, halogen and cyano, wherein the phenyl groups may be optionally mono- to tri-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; and R is C₁₋₆-alkyl, C₂₋₆-alkenyl or C₅₋₆-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkoxycarbonyl, C₁₋₄haloalkyl, halogen and cyano.
 5. A compound of formula I according to claim 1 wherein A is phenyl or naphthyl, each optionally-substituted by 1 to 3 substituents selected from the group comprising C₁₋₄-alkyl, C₂₋₆-alkenyl, C₃₋₆-cycloalkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-alkoxycarbonyl, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen, nitro and cyano; or from the group comprising aryl, aryloxy or arylthio, wherein each of the groups may be substituted with halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy or C₁₋₄-alkylthio; and B is a direct bond, methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or 2,2-propylene; and E is a group

 wherein R₂ is C₁₋₄-alkyl, and R₃ is C₁₋₈-alkyl, C₃₋₈-alkenyl, C₃₋₈-alkynyl, phenyl-C₁₋₆-alkyl, phenyl-C₃₋₆-alkenyl, phenyl-C₃₋₀-alkynyl, C₃₋₈-cycloalkyl-C₃₋₈-alkynyl, C₁₋₈-halogenalkyl or C₃₋₈-halogenalkenyl wherein in each of the preceding radicals the phenyl groups may be optionally substituted with 1 to 3 substituents selected from the group comprising C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkyl, C₁₋₄-haloalkoxy, C₁₋₄-haloalkylthio, halogen and cyano; and R is straight-chain or branched C₁₋₄-alkyl, C₂₋₆-alkenyl or C₅₋₆-cycloalkyl, wherein each of the preceding groups may be optionally mono- or poly-substituted with F, Cl or Br; and T is NH.
 6. A composition for controlling and protecting against phytopathogenic microorganisms, comprising a compound of formula I according to claim 1 as active ingredient together with a suitable carrier.
 7. A method of controlling and preventing an infestation of crop plants by phytopathogenic microorganisms, which comprises the application of a compound of formula I according to claim 1 as active ingredient to the plant, to parts of plants or to the locus thereof.
 8. A method according to claim 7, wherein the phytopathogenic microorganisms are fungal organisms.
 9. A compound according to claim 1 selected from the group consisting of 2-(3,4-dichloro-phenyl)-N-[2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-2-methylthiolmino-acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; N-[2-(4-allyloxy-3-methoxy-phenyl)-ethyl]-2-(3,4-dichloro-phenyl)-2-methylthiolmino-acetamide; N-[2-(3-methoxy-4-prop-ynyloxy-phenyl)-ethyl]-2-methylthiolmino-2-(4-tolyl )-acetamide; 2-C4-bromo-phenyl)-N-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide; N-[2-(3-methoxy-4-prop-ynyloxy-phenyl)-ethyl]-2-naphthalen-2-yl-2-methylthioimino-2-acetamide; 2-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2-(4-methoxy-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-methylthioimino-acetamide; N-[2-(3-methoxy-4-prop-ynyloxy-phenyl)-ethyl]-2-(3,4-dichloro-phenyl)-2-ethylthioimino-2-(4-tolyl)-acetamide; 2-[4-(4-methyl-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2-[4-(3,4-dichloro-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2-[4-(4-chloro-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthioimino-acetamide; 2-[4-(4-trifluoromethyl-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2-[4-(4-trifluoromethoxy-phenyl)-phenyl]-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthiolmino-acetamide; 2-[4-(4-tert.-butyl-phenyl)-phenyl]-N-[2-(3,4-di-methoxyphenyl)-ethyl]-2-methylthiolmino-acetamide; and 2-(4-biphenylyl)-N-[2-(3,4-di-methoxy-phenyl)-ethyl]-2-methylthiolmino-acetamide. 